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molecular formula C14H18N4O3 B562225 Trimethoprim-d9 (Major) CAS No. 1189460-62-5

Trimethoprim-d9 (Major)

Cat. No. B562225
M. Wt: 299.378
InChI Key: IEDVJHCEMCRBQM-GQALSZNTSA-N
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Patent
US04144263

Procedure details

α-Diethoxymethyl-α-formyl-β-(3,4,5-trimethoxyphenyl) propionitrile (35.1 g, 0.10 mol) was added to an ethanolic solution of guanidine (from 0.35 mol of guanidine hydrochloride). The mixture was heated at reflux for a total of 6.5 hours during which time enough ethanol was allowed to boil off to bring the reaction temperature up to 85°. The dark solution was allowed to cool and stand overnight. The mixture was filtered, and the solid was washed with cold ethanol and dried to yield crude product (24.4 g, 84.1%). Purification was effected by dissolving the crude product in hot aqueous acetic acid and reprecipitation with concentrated ammonium hydroxide. The precipitate was washed twice with water, once with cold acetone, and dried to yield 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (19.5 g, 67.2%), m.p. 197°-198° C. (identity confirmed by nmr). The acetone was concentrated in vacuo to dryness yielding additional though somewhat less pure trimethoprim (2,5 g, 8.6%, m.p. 194°-196° C.).
Name
α-Diethoxymethyl-α-formyl-β-(3,4,5-trimethoxyphenyl) propionitrile
Quantity
35.1 g
Type
reactant
Reaction Step One
Quantity
0.35 mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

Identifiers

REACTION_CXSMILES
C(OC(OCC)[C:5]([CH:21]=O)([CH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1)[C:6]#[N:7])C.[NH2:26][C:27]([NH2:29])=[NH:28]>C(O)C>[NH2:29][C:27]1[N:28]=[C:6]([NH2:7])[C:5]([CH2:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:21][N:26]=1

Inputs

Step One
Name
α-Diethoxymethyl-α-formyl-β-(3,4,5-trimethoxyphenyl) propionitrile
Quantity
35.1 g
Type
reactant
Smiles
C(C)OC(C(C#N)(CC1=CC(=C(C(=C1)OC)OC)OC)C=O)OCC
Name
Quantity
0.35 mol
Type
reactant
Smiles
NC(=N)N
Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The mixture was heated
CUSTOM
Type
CUSTOM
Details
up to 85°
TEMPERATURE
Type
TEMPERATURE
Details
to cool
FILTRATION
Type
FILTRATION
Details
The mixture was filtered
WASH
Type
WASH
Details
the solid was washed with cold ethanol
CUSTOM
Type
CUSTOM
Details
dried
CUSTOM
Type
CUSTOM
Details
to yield crude product (24.4 g, 84.1%)
CUSTOM
Type
CUSTOM
Details
Purification
DISSOLUTION
Type
DISSOLUTION
Details
by dissolving
CUSTOM
Type
CUSTOM
Details
the crude product in hot aqueous acetic acid and reprecipitation with concentrated ammonium hydroxide
WASH
Type
WASH
Details
The precipitate was washed twice with water, once with cold acetone
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
8 (± 8) h
Name
Type
product
Smiles
NC1=NC=C(C(=N1)N)CC1=CC(=C(C(=C1)OC)OC)OC
Measurements
Type Value Analysis
AMOUNT: MASS 19.5 g
YIELD: PERCENTYIELD 67.2%
YIELD: CALCULATEDPERCENTYIELD 67.2%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04144263

Procedure details

α-Diethoxymethyl-α-formyl-β-(3,4,5-trimethoxyphenyl) propionitrile (35.1 g, 0.10 mol) was added to an ethanolic solution of guanidine (from 0.35 mol of guanidine hydrochloride). The mixture was heated at reflux for a total of 6.5 hours during which time enough ethanol was allowed to boil off to bring the reaction temperature up to 85°. The dark solution was allowed to cool and stand overnight. The mixture was filtered, and the solid was washed with cold ethanol and dried to yield crude product (24.4 g, 84.1%). Purification was effected by dissolving the crude product in hot aqueous acetic acid and reprecipitation with concentrated ammonium hydroxide. The precipitate was washed twice with water, once with cold acetone, and dried to yield 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (19.5 g, 67.2%), m.p. 197°-198° C. (identity confirmed by nmr). The acetone was concentrated in vacuo to dryness yielding additional though somewhat less pure trimethoprim (2,5 g, 8.6%, m.p. 194°-196° C.).
Name
α-Diethoxymethyl-α-formyl-β-(3,4,5-trimethoxyphenyl) propionitrile
Quantity
35.1 g
Type
reactant
Reaction Step One
Quantity
0.35 mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

Identifiers

REACTION_CXSMILES
C(OC(OCC)[C:5]([CH:21]=O)([CH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1)[C:6]#[N:7])C.[NH2:26][C:27]([NH2:29])=[NH:28]>C(O)C>[NH2:29][C:27]1[N:28]=[C:6]([NH2:7])[C:5]([CH2:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:21][N:26]=1

Inputs

Step One
Name
α-Diethoxymethyl-α-formyl-β-(3,4,5-trimethoxyphenyl) propionitrile
Quantity
35.1 g
Type
reactant
Smiles
C(C)OC(C(C#N)(CC1=CC(=C(C(=C1)OC)OC)OC)C=O)OCC
Name
Quantity
0.35 mol
Type
reactant
Smiles
NC(=N)N
Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The mixture was heated
CUSTOM
Type
CUSTOM
Details
up to 85°
TEMPERATURE
Type
TEMPERATURE
Details
to cool
FILTRATION
Type
FILTRATION
Details
The mixture was filtered
WASH
Type
WASH
Details
the solid was washed with cold ethanol
CUSTOM
Type
CUSTOM
Details
dried
CUSTOM
Type
CUSTOM
Details
to yield crude product (24.4 g, 84.1%)
CUSTOM
Type
CUSTOM
Details
Purification
DISSOLUTION
Type
DISSOLUTION
Details
by dissolving
CUSTOM
Type
CUSTOM
Details
the crude product in hot aqueous acetic acid and reprecipitation with concentrated ammonium hydroxide
WASH
Type
WASH
Details
The precipitate was washed twice with water, once with cold acetone
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
8 (± 8) h
Name
Type
product
Smiles
NC1=NC=C(C(=N1)N)CC1=CC(=C(C(=C1)OC)OC)OC
Measurements
Type Value Analysis
AMOUNT: MASS 19.5 g
YIELD: PERCENTYIELD 67.2%
YIELD: CALCULATEDPERCENTYIELD 67.2%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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