Dimethylformamide → Ethyl 2-(4,6-dimethoxypyrimidin-2-yl)thio2-(1-cyclopentenyl)acetate

HRID 1073030Notes

Reaction equation

HRID 1073030 reaction equation
[SH:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[C:12]1([CH:17](OS(C)(=O)=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:15][CH2:14][CH:13]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([S:1][CH:17]([C:12]2[CH2:16][CH2:15][CH2:14][CH:13]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 15070290Ethyl 2-(1-cyclopentenyl)-2-(methylsulfonyloxy)acetateHCID 178493561HCID 178493561, compound

Product 1

HCID 15070291Ethyl 2-(4,6-dimethoxypyrimidin-2-yl)thio2-(1-cyclopentenyl)acetateYield 49.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.4 g of 2-mercapto-4,6-dimethoxypyrimidine, 15.0 g of ethyl 2-(1-cyclopentenyl)-2-(methylsulfonyloxy)acetate, 100 ml of N,N-dimethylformamide and 9.2 g of anhydrous potassium carbonate were stirred at 90° C. for 5 hours. The reaction mixture was cooled to room temperature and then diluted with water. The aqueous mixture was extracted with ethyl ether. The ethyl ether extract was washed with water and dried. Then, ethyl ether was removed by distillation under reduced pressure to obtain an yellow oily substance. The yellow oily substance was purified by silica gel column chromatography (eluent: hexane/ethyl acetate =10/1) to obtain 9.7 g of the desired product.

Workup

  1. extractionThe aqueous mixture was extracted with ethyl ether
  2. extractionThe ethyl ether extract
  3. washwas washed with water
  4. customdried
  5. customThen, ethyl ether was removed by distillation under reduced pressure
  6. customto obtain an yellow oily substance
  7. customThe yellow oily substance was purified by silica gel column chromatography (eluent: hexane/ethyl acetate =10/1)

Sources & evidence

ORD record
ord-ecca0ee3c087430696aec940157989d7
Source dataset
uspto-grants-1990_11
Patent number
US04968340

Reaction notes

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