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molecular formula C5H12O B152257 2-Methyl-2-butanol CAS No. 75-85-4

2-Methyl-2-butanol

Cat. No. B152257
M. Wt: 88.15 g/mol
InChI Key: MSXVEPNJUHWQHW-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US09434698B2

Procedure details

Palladium acetate (0.0018 g, 8.09 μmol), di-tert-butyl(2′,4′,6′-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (0.0086 g, 0.018 mmol) and water (0.6 μL, 0.032 mmol) were charged to a 40-mL reaction vial inside an inert atmosphere glove box. tert-Amyl alcohol (1.0 mL) was added, and the contents were heated to 80° C. and stirred at this temperature for 15 minutes. The reaction mixture was cooled down to room temperature. Potassium phosphate tribasic (0.094 g, 0.445 mmol), 6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl methanesulfonate (0.2 g, 0.404 mmol), methanesulfonamide (0.046 g, 0.485 mmol) and tert-amyl alcohol (1.5 mL) were added to the 40-mL reaction vial. The reaction temperature was raised to 110° C., and the contents were stirred for 14 hours. HPLC analysis of the reaction mixture showed that the titled compound was formed in 5 area % at 210 nm.
Quantity
1 mL
Type
reactant
Reaction Step One
Name
Potassium phosphate tribasic
Quantity
0.094 g
Type
reactant
Reaction Step Two
Name
6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl methanesulfonate
Quantity
0.2 g
Type
reactant
Reaction Step Two
Quantity
0.046 g
Type
reactant
Reaction Step Two
Quantity
1.5 mL
Type
reactant
Reaction Step Two
Quantity
0.0086 g
Type
reactant
Reaction Step Three
Name
Quantity
0.6 μL
Type
reactant
Reaction Step Three
Quantity
0.0018 g
Type
catalyst
Reaction Step Three

Identifiers

REACTION_CXSMILES
C(P(C(C)(C)C)C1C(OC)=CC=C(OC)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.O.C(O)(CC)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CS(O[C:55]1[CH:64]=[CH:63][C:62]2[C:57](=[CH:58][CH:59]=[C:60]([C:65]3[CH:70]=[C:69]([N:71]4[CH:76]=[CH:75][C:74](=[O:77])[NH:73][C:72]4=[O:78])[CH:68]=[C:67]([C:79]([CH3:82])([CH3:81])[CH3:80])[C:66]=3[O:83][CH3:84])[CH:61]=2)[CH:56]=1)(=O)=O.[CH3:85][S:86]([NH2:89])(=[O:88])=[O:87]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:79]([C:67]1[C:66]([O:83][CH3:84])=[C:65]([C:60]2[CH:61]=[C:62]3[C:57](=[CH:58][CH:59]=2)[CH:56]=[C:55]([NH:89][S:86]([CH3:85])(=[O:88])=[O:87])[CH:64]=[CH:63]3)[CH:70]=[C:69]([N:71]2[CH:76]=[CH:75][C:74](=[O:77])[NH:73][C:72]2=[O:78])[CH:68]=1)([CH3:82])([CH3:81])[CH3:80] |f:3.4.5.6,9.10.11|

Inputs

Step One
Name
Quantity
1 mL
Type
reactant
Smiles
C(C)(C)(CC)O
Step Two
Name
Potassium phosphate tribasic
Quantity
0.094 g
Type
reactant
Smiles
[O-]P(=O)([O-])[O-].[K+].[K+].[K+]
Name
6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl methanesulfonate
Quantity
0.2 g
Type
reactant
Smiles
CS(=O)(=O)OC1=CC2=CC=C(C=C2C=C1)C1=C(C(=CC(=C1)N1C(NC(C=C1)=O)=O)C(C)(C)C)OC
Name
Quantity
0.046 g
Type
reactant
Smiles
CS(=O)(=O)N
Name
Quantity
1.5 mL
Type
reactant
Smiles
C(C)(C)(CC)O
Step Three
Name
Quantity
0.0086 g
Type
reactant
Smiles
C(C)(C)(C)P(C1=C(C(=CC=C1OC)OC)C1=C(C=C(C=C1C(C)C)C(C)C)C(C)C)C(C)(C)C
Name
Quantity
0.6 μL
Type
reactant
Smiles
O
Name
Quantity
0.0018 g
Type
catalyst
Smiles
C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-]

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
80 °C
Stirring
Type
CUSTOM
Details
stirred at this temperature for 15 minutes
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was cooled down to room temperature
TEMPERATURE
Type
TEMPERATURE
Details
The reaction temperature was raised to 110° C.
STIRRING
Type
STIRRING
Details
the contents were stirred for 14 hours
Duration
14 h

Outcomes

Product
Details
Reaction Time
15 min
Name
Type
product
Smiles
C(C)(C)(C)C=1C(=C(C=C(C1)N1C(NC(C=C1)=O)=O)C=1C=C2C=CC(=CC2=CC1)NS(=O)(=O)C)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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