Dimethylformamide → 4,4-Difluoro-3-methyl-3-butenyl 4-methyl-2-(methylthio)pyrimidine-5-carboxylate

HRID 917376Notes

Reaction equation

HRID 917376 reaction equation
CN(C)C=O.CS([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:16])[F:15])(=O)=O.[CH3:18][C:19]1[C:24]([C:25](O)=[O:26])=[CH:23][N:22]=[C:21]([S:28][CH3:29])[N:20]=1.C(=O)([O-])O.[Na+]>O>[CH3:18][C:19]1[C:24]([C:25]([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:15])[F:16])=[O:26])=[CH:23][N:22]=[C:21]([S:28][CH3:29])[N:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 36133564-Methyl-2-(methylsulfanyl)pyrimidine-5-carboxylic acidHCID 230202374,4-Difluoro-3-Methyl-3-Buten-1-Yl Methanesulfonate

Product 1

HCID 691788864,4-Difluoro-3-methyl-3-butenyl 4-methyl-2-(methylthio)pyrimidine-5-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 40 ml of N,N-dimethylformamide were dissolved 4.00 g (20 mmol) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate and 4.00 g (22 mmol) of 4-methyl-2-(methylthio)pyrimidine-5-carboxylic acid, followed by the addition of 3.70 g (44 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with diethyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate, the addition of “Florisil” and filtering. The solution was concentrated under reduced pressure to obtain 5.30 g (yield: 92%) of 4,4-difluoro-3-methyl-3-butenyl 4-methyl-2-(methylthio)-pyrimidine-5-carboxylate.

Workup

  1. customThe reaction liquid
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. additionthe addition of “Florisil”
  6. filtrationfiltering
  7. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-01f56c091911419a9c3ab4d554ebb560
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

Loading…