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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

A solution of α-carbethoxy-α-diethoxymethyl-β-(3,4,5-trimethoxyphenyl)propionitrile (7.9 g, 0.02 mol) and an equivalent amount of potassium hydroxide in ethanol (50 ml) was heated at reflux for one hour. A solution of guanidine (0.07 mol) in ethanol (50 ml) was added, and reflux was resumed. Some ethanol was allowed to boil off bringing the reaction temperature up to 85°. After about 20 hours at reflux the mixture was allowed to cool, and the product was filtered and washed with ethanol. The crude product was purified by treating with hot aqueous acetic acid and reprecipitation with ammonium hydroxide. The yield of purified trimethoprim (m.p. 197°-198°) was 3.6g (62%), its identity being confirmed by an NMR spectrum.
Name
α-carbethoxy-α-diethoxymethyl-β-(3,4,5-trimethoxyphenyl)propionitrile
Quantity
7.9 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
50 mL
Type
solvent
Reaction Step One
Quantity
0.07 mol
Type
reactant
Reaction Step Two
Quantity
50 mL
Type
solvent
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
C([C:6]([CH:22](OCC)OCC)([CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=1)[C:7]#[N:8])(OCC)=O.[OH-].[K+].[NH2:31][C:32]([NH2:34])=[NH:33]>C(O)C>[NH2:34][C:32]1[N:33]=[C:7]([NH2:8])[C:6]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:22][N:31]=1 |f:1.2|

Inputs

Step One
Name
α-carbethoxy-α-diethoxymethyl-β-(3,4,5-trimethoxyphenyl)propionitrile
Quantity
7.9 g
Type
reactant
Smiles
C(=O)(OCC)C(C#N)(CC1=CC(=C(C(=C1)OC)OC)OC)C(OCC)OCC
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
50 mL
Type
solvent
Smiles
C(C)O
Step Two
Name
Quantity
0.07 mol
Type
reactant
Smiles
NC(=N)N
Name
Quantity
50 mL
Type
solvent
Smiles
C(C)O
Step Three
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
at reflux for one hour
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
reflux
CUSTOM
Type
CUSTOM
Details
up to 85°
TEMPERATURE
Type
TEMPERATURE
Details
After about 20 hours at reflux the mixture
Duration
20 h
TEMPERATURE
Type
TEMPERATURE
Details
to cool
FILTRATION
Type
FILTRATION
Details
the product was filtered
WASH
Type
WASH
Details
washed with ethanol
CUSTOM
Type
CUSTOM
Details
The crude product was purified
ADDITION
Type
ADDITION
Details
by treating with hot aqueous acetic acid and reprecipitation with ammonium hydroxide

Outcomes

Product
Name
Type
Smiles
NC1=NC=C(C(=N1)N)CC1=CC(=C(C(=C1)OC)OC)OC

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

A solution of α-carbethoxy-α-diethoxymethyl-β-(3,4,5-trimethoxyphenyl)propionitrile (7.9 g, 0.02 mol) and an equivalent amount of potassium hydroxide in ethanol (50 ml) was heated at reflux for one hour. A solution of guanidine (0.07 mol) in ethanol (50 ml) was added, and reflux was resumed. Some ethanol was allowed to boil off bringing the reaction temperature up to 85°. After about 20 hours at reflux the mixture was allowed to cool, and the product was filtered and washed with ethanol. The crude product was purified by treating with hot aqueous acetic acid and reprecipitation with ammonium hydroxide. The yield of purified trimethoprim (m.p. 197°-198°) was 3.6g (62%), its identity being confirmed by an NMR spectrum.
Name
α-carbethoxy-α-diethoxymethyl-β-(3,4,5-trimethoxyphenyl)propionitrile
Quantity
7.9 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
50 mL
Type
solvent
Reaction Step One
Quantity
0.07 mol
Type
reactant
Reaction Step Two
Quantity
50 mL
Type
solvent
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
C([C:6]([CH:22](OCC)OCC)([CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=1)[C:7]#[N:8])(OCC)=O.[OH-].[K+].[NH2:31][C:32]([NH2:34])=[NH:33]>C(O)C>[NH2:34][C:32]1[N:33]=[C:7]([NH2:8])[C:6]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:22][N:31]=1 |f:1.2|

Inputs

Step One
Name
α-carbethoxy-α-diethoxymethyl-β-(3,4,5-trimethoxyphenyl)propionitrile
Quantity
7.9 g
Type
reactant
Smiles
C(=O)(OCC)C(C#N)(CC1=CC(=C(C(=C1)OC)OC)OC)C(OCC)OCC
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
50 mL
Type
solvent
Smiles
C(C)O
Step Two
Name
Quantity
0.07 mol
Type
reactant
Smiles
NC(=N)N
Name
Quantity
50 mL
Type
solvent
Smiles
C(C)O
Step Three
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
at reflux for one hour
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
reflux
CUSTOM
Type
CUSTOM
Details
up to 85°
TEMPERATURE
Type
TEMPERATURE
Details
After about 20 hours at reflux the mixture
Duration
20 h
TEMPERATURE
Type
TEMPERATURE
Details
to cool
FILTRATION
Type
FILTRATION
Details
the product was filtered
WASH
Type
WASH
Details
washed with ethanol
CUSTOM
Type
CUSTOM
Details
The crude product was purified
ADDITION
Type
ADDITION
Details
by treating with hot aqueous acetic acid and reprecipitation with ammonium hydroxide

Outcomes

Product
Name
Type
Smiles
NC1=NC=C(C(=N1)N)CC1=CC(=C(C(=C1)OC)OC)OC

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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