Dimethylformamide → 2-tert-Butyl-4-chloro-6-(trifluoromethyl)pyrimidine

HRID 1018923Notes

Reaction equation

HRID 1018923 reaction equation
S(Cl)([Cl:3])=O.CN(C=O)C.[C:10]([C:14]1[N:19]=[C:18](O)[CH:17]=[C:16]([C:21]([F:24])([F:23])[F:22])[N:15]=1)([CH3:13])([CH3:12])[CH3:11]>ClCCl>[C:10]([C:14]1[N:19]=[C:18]([Cl:3])[CH:17]=[C:16]([C:21]([F:24])([F:23])[F:22])[N:15]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178441869HCID 178441869, compound

Product 1

HCID 158374832-tert-Butyl-4-chloro-6-(trifluoromethyl)pyrimidineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Firstly 86.5 ml of thionyl chloride and then 8 ml of DMF were added dropwise to a solution of 60 g (0.27 mol) of 2-t-butyl-4-hydroxy-6-trifluoromethylpyrimidine in 800 ml of dichloromethane, and then the mixture was refluxed. The volatile constituents were removed under reduced pressure, the residue was taken up in 100 ml of dichloromethane, the pH was adjusted to 7 with saturated NaHCO3 solution and, after workup by extraction, 67 g (96%) of a clear oil were obtained.

Workup

  1. temperaturethe mixture was refluxed
  2. customThe volatile constituents were removed under reduced pressure
  3. extractionafter workup by extraction

Sources & evidence

ORD record
ord-e73307536edf4fe3b7c5451e4ba73b48
Source dataset
uspto-grants-2002_11
Patent number
US06486162B2

Reaction notes

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