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

HRID 1779354Notes

Reaction equation

HRID 1779354 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 3 N 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 3 N HCl (2×25 mL,), saturated sodium bicarbonate (25 mL) and brine
  3. customdried
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-eef12819bcf74c4cae0c219e582f3550
Source dataset
uspto-grants-1997_05
Patent number
US05627174

Reaction notes

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