Dimethylformamide → HCID 69182348, compound

HRID 917375Notes

Reaction equation

HRID 917375 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.[CH2:18]([C:25]1[N:30]=[C:29]([CH3:31])[C:28]([C:32](O)=[O:33])=[CH:27][N:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>O>[CH2:18]([C:25]1[N:30]=[C:29]([CH3:31])[C:28]([C:32]([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:16])[F:15])=[O:33])=[CH:27][N:26]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 230202374,4-Difluoro-3-Methyl-3-Buten-1-Yl MethanesulfonateHCID 23020286HCID 23020286, compound

Product 1

HCID 69182348HCID 69182348, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 10 ml of N,N-dimethylformamide were dissolved 1.00 g (5.0 mmol) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate and 1.30 g (5.5 mmol) of 2-benzyl-4-methylpyrimidine-5-carboxylic acid, followed by the addition of 0.50 g (6.0 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 an hydrous magnesium sulfate, the addition of “Florisil” and filtering. The solution was concentrated under reduced pressure to obtain 1.30 g (yield: 78%) of 4,4-difluoro-3-methyl-3-butenyl 2-benzyl-4-methylpyrimidine-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 an hydrous magnesium sulfate
  5. additionthe addition of “Florisil”
  6. filtrationfiltering
  7. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3a89dca5e878435abceb539da2615cff
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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