Water → Ethyl 3-(difluoromethyl)-1-(5-fluoropyrimidin-2-yl)-1H-pyrazole-4-carboxylate

HRID 2279612Notes

Reaction equation

HRID 2279612 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([CH:11]([F:13])[F:12])=[N:4]1)C.ClC1[N:20]=[CH:19][C:18]([F:21])=[CH:17][N:16]=1.C([O-])([O-])=O.[K+].[K+].O.CN1C(=O)C[CH2:32][CH2:31]1>>[F:12][CH:11]([F:13])[C:5]1[C:6]([C:8]([O:10][CH2:31][CH3:32])=[O:9])=[CH:7][N:3]([C:1]2[N:20]=[CH:19][C:18]([F:21])=[CH:17][N:16]=2)[N:4]=1

Participants

6

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 5834662-Chloro-5-fluoropyrimidineHCID 67194762ethyl 3-(difluoromethyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 59579960Ethyl 3-(difluoromethyl)-1-(5-fluoropyrimidin-2-yl)-1H-pyrazole-4-carboxylate

Procedure

A solution of ethyl 3-(difluoromethyl)-1H-pyrazole-4-carboxylic acid (190 mg, 1.0 mmol), 2-chloro-5-fluoro-pyrimidine (132 mg, 1.0 mmol) and K2CO3 (276 mg, 2.0 mmol) in NMP (2.0 mL) is heated in a microwave reactor at 150° C. for 1 h. The mixture is poured into H2O, extracted with EtOAc (3×25 mL) and dried over anhydrous MgSO4. The crude product is purified by silica gel column chromatography using 15-25% EtOAc/hexane to afford the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dd2b6313eb2140a8b111d1c51dfb42e7
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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