Water → HCID 20095263, compound

HRID 1768918Notes

Reaction equation

HRID 1768918 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[C:12]([S:17][C:18]3[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:34]([O:40][CH2:41]Cl)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36].O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16][CH2:41][O:40][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:15])=[C:12]([S:17][C:18]3[N:19]=[C:20]([O:26][CH3:27])[CH:21]=[C:22]([O:24][CH3:25])[N:23]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 20095262HCID 20095262, compound

Product 1

HCID 20095263HCID 20095263, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.70 g (0.0019 mol) of 4-(4-fluorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinic acid and 0.50 g (0.0036 mol) of potassium carbonate in 10 ml of N,N-dimethylformamide was stirred at room temperature for 1 hour. Thereafter, 0.34 g (0.0022 mol) of chloromethyl pivalate was further added to the resultant mixture, and the mixture was stirred at room temperature for 2 hours. The mixture was then poured into water, and extracted with 50 ml of ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and concentrated. The concentrate was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/4) to obtain 0.81 g of a yellowish thick syrup-like aimed product.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionextracted with 50 ml of ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-f79c0e354b3f4bd18b483befa19058db
Source dataset
uspto-grants-1995_01
Patent number
US05380700

Reaction notes

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