Dimethylformamide → 4,4-difluoro-3-methyl-3-butenyl 2-(N-butyl-N-methylamino)-4-methylpyrimidine-5-carboxylate

HRID 917378Notes

Reaction equation

HRID 917378 reaction equation
CN(C)C=O.CS([C:10]1[N:15]=[C:14]([CH3:16])[C:13]([C:17]([O:19][CH2:20][CH2:21][C:22]([CH3:26])=[C:23]([F:25])[F:24])=[O:18])=[CH:12][N:11]=1)(=O)=O.[CH2:27]([NH:31][CH3:32])[CH2:28][CH2:29][CH3:30]>O>[CH2:27]([N:31]([C:10]1[N:15]=[C:14]([CH3:16])[C:13]([C:17]([O:19][CH2:20][CH2:21][C:22]([CH3:26])=[C:23]([F:25])[F:24])=[O:18])=[CH:12][N:11]=1)[CH3:32])[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8068N-MethylbutylamineHCID 691816824,4-Difluoro-3-methyl-3-butenyl 2-methanesulfonyl-4-methylpyrimidine-5-carboxylate

Product 1

HCID 691822964,4-difluoro-3-methyl-3-butenyl 2-(N-butyl-N-methylamino)-4-methylpyrimidine-5-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3 ml of N,N-dimethylformamide were dissolved 0.50 g (1.6 mmol) of 4,4-difluoro-3-methyl-3-butenyl 2-methanesulfonyl-4-methylpyrimidine-5-carboxylate, followed by the addition of 0.28 g (3.2 mmol) of N-butyl-N-methylamine and stirring at room temperature for 30 minutes. 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 and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate ether:hexane=1:7) to obtain 0.41 g (yield: 80%) of 4,4-difluoro-3-methyl-3-butenyl 2-(N-butyl-N-methylamino)-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 anhydrous magnesium sulfate and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (ethyl acetate ether:hexane=1:7)

Sources & evidence

ORD record
ord-902c14b103ff4726a2055043bd4326fe
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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