Potassium Carbonate → 2-(3,4,4-Trifluoro-1-oxo-3-butenyl)amino-4,6-dimethoxy-pyrimidine

HRID 1940839Notes

Reaction equation

HRID 1940839 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19](=[C:24]([F:26])[F:25])[CH2:20][C:21](Cl)=[O:22]>ClCCl.O>[F:18][C:19](=[C:24]([F:26])[F:25])[CH2:20][C:21]([NH:1][C:2]1[N:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[N:7]=1)=[O:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 109207893,4,4-Trifluoro-3-butenoyl chloride

Product 1

HCID 153350272-(3,4,4-Trifluoro-1-oxo-3-butenyl)amino-4,6-dimethoxy-pyrimidineYield 10.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled stirred suspension of 2-amino-4,6-dimethoxypyrimidine (1.55 g, 10 mmol) in dichloromethane (50 mL) and potassium carbonate (2.76 g, 20 mmol) in water (20 mL) was added 3,4,4-trifluoro-3-butenoyl chloride (3.17 g, 20 mmol). The reaction mixture was stirred in cold for 10 min and at r.t. for 15 min. The organic layer was washed with 3N HCl (2×25 mL), saturated sodium bicarbonate (25 mL) and brine, and dried. Evaporation of the solvent gave 0.296 g (10%) of the title compound as a white solid, m.p. 127°-130° C.

Workup

  1. stirringThe reaction mixture was stirred in cold for 10 min
  2. washThe organic layer was washed with 3N HCl (2×25 mL), saturated sodium bicarbonate (25 mL) and brine
  3. customdried
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-370d746bf3944720a2af8aaf6477ebe1
Source dataset
uspto-grants-1997_12
Patent number
US05700840

Reaction notes

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