Thiophenol → HCID 23020229, compound

HRID 917379Notes

Reaction equation

HRID 917379 reaction equation
O1CCCC1.[CH3:6][S:7]([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.[C:27]1(S)[CH:32]=[CH:31]C=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:16][C:14]1[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]=[C:10]([S:7][C:6]2[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=2)[N:15]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 691816824,4-Difluoro-3-methyl-3-butenyl 2-methanesulfonyl-4-methylpyrimidine-5-carboxylate

Product 1

HCID 23020229HCID 23020229, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 ml of tetrahydrofuran were dissolved 0.56 g (1.8 mmol) of 4,4-difluoro-3-methyl-3-butenyl 2-methanesulfonyl-4-methylpyrimidine-5-carboxylate and 0.21 g (1.9 mmol) of thiophenol, followed by the addition of 0.30 g (2.8 mmol) of sodium carbonate and stirring at room temperature for 1 hour. 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:hexane=1:8) to obtain 0.54 g (yield: 88%) of 4,4-difluoro-3-methyl-3-butenyl 4-methyl-2-(phenylthio)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 and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:8)

Sources & evidence

ORD record
ord-0a93905a50e543ea9b1f5df55e47d14e
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

Loading…