Ammonia → 4-Chloro-5-(trifluoromethyl)pyrimidin-2-amine

HRID 2093295Notes

Reaction equation

HRID 2093295 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH3:13]>>[NH2:13][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

Product 1

HCID 219231104-Chloro-5-(trifluoromethyl)pyrimidin-2-amineYield 45%

Conditions

Temperature
5 °C

Procedure

With stirring, 1.0 g of 2,4-dichloro-5-(trifluoromethyl)pyrimidine, Aldrich order no. 684864, is added to a methanolic ammonia solution (ca. 8 mol of ammonia in methanol) cooled to ca. 5° C., the mixture is heated to 25° C. and stirred for 2 hours at this temperature. The mixture is concentrated by evaporation and added to water. After filtering off with suction, 0.56 g of a mixture of 4-amino-2-chloro-5-trifluoromethylpyrimidine (ca. 45%) and 2-amino-4-chloro-5-trifluoromethylpyrimidine (ca. 45%) is obtained.

Workup

  1. temperaturethe mixture is heated to 25° C.
  2. stirringstirred for 2 hours at this temperature
  3. concentrationThe mixture is concentrated by evaporation
  4. additionadded to water
  5. filtrationAfter filtering off with suction, 0.56 g of a mixture of 4-amino-2-chloro-5-trifluoromethylpyrimidine (ca. 45%)

Sources & evidence

ORD record
ord-fa2ad0997f144a21a66ad18d33737e02
Source dataset
uspto-grants-2013_05
Patent number
US08445408B2

Reaction notes

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