Réaction #1042

ord-7acdd14915da464f89faabd34f59b6eb

Équation de réaction

O=C(Cl)CC(F)=C(F)F
3,4,4-trifluoro-3-butenoyl chloride
COc1cc(OC)nc(N)n1
2-amino-4,6-dimethoxypyrimidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
COc1cc(OC)nc(NC(=O)CC(F)=C(F)F)n1
title compound
Rendement 10.7%
COc1cc(OC)nc(NC(=O)CC(F)=C(F)F)n1
2-(3,4,4-trifluoro-1-oxo-3-butenyl)amino-4,6-dimethoxy-pyrimidine
Rendement 10.7%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.STIRRINGThe reaction mixture was stirred in cold for 10 min
  2. 2
    LavageThe organic layer was washed with 3N HCl (2×25 mL), saturated sodium bicarbonate (25 mL) and brine
  3. 3
    Autredried
  4. 4
    AutreEvaporation of the solvent

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05723470uspto-grants-1998_03