Sodium Hydroxide → N-benzyl-6-chloro-N-(2,2,2-trifluoroethyl)pyrimidine-4-carboxamide

HRID 1640237

Reaction equation

HRID 1640237 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]([F:13])([F:12])[F:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:16][C:17]1[N:22]=[CH:21][N:20]=[C:19]([C:23](Cl)=[O:24])[CH:18]=1.C(=O)([O-])O.[Na+]>ClCCl.C(O)C>[CH2:1]([N:8]([CH2:9][C:10]([F:12])([F:11])[F:13])[C:23]([C:19]1[CH:18]=[C:17]([Cl:16])[N:22]=[CH:21][N:20]=1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 4962181Benzyl-(2,2,2-trifluoro-ethyl)-amineHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 58117522N-benzyl-6-chloro-N-(2,2,2-trifluoroethyl)pyrimidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.04 g (5.5 mmol) benzyl-(2,2,2-trifluoroethyl)-amine and 5.5 mL (5.5 mmol) of a 1M sodium hydroxide solution were added dropwise to 1.0 g (5.65 mmol) 6-chloropyrimidine-4-carboxylic acid chloride in 20 mL dichloromethane while cooling with a bath of ice and ethanol. The mixture was first stirred for 2 h with cooling and then for 1 h at RT. 50 mL of a saturated sodium hydrogen carbonate solution were added and the mixture was stirred for 10 min. The organic phase was separated off, washed with water and 1M hydrochloric acid, dried on sodium sulphate, filtered and evaporated down i.vac.

Workup

  1. temperaturewith cooling
  2. waitfor 1 h at RT
  3. stirringthe mixture was stirred for 10 min
  4. customThe organic phase was separated off
  5. washwashed with water and 1M hydrochloric acid
  6. customdried on sodium sulphate
  7. filtrationfiltered
  8. customevaporated down i.vac

Sources & evidence

ORD record
ord-da8810868e5143c0aaef79dde8ed6ea1
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Linked notes

Loading…