Dimethylformamide → 2-Amino-4-methyl-6-(1,1,2-trifluoro-2-chloro-ethoxy)-pyrimidine

HRID 2309167Notes

Reaction equation

HRID 2309167 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Cl:10][C:11]([F:15])=[C:12]([F:14])[F:13].[OH-].[K+].CN(C)C=O>O.C(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([CH3:9])[CH:5]=[C:6]([O:8][C:12]([F:14])([F:13])[CH:11]([F:15])[Cl:10])[N:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6594ChlorotrifluoroethyleneHCID 14797Potassium HydroxideHCID 178429408HCID 178429408, compound

Product 1

HCID 201856922-Amino-4-methyl-6-(1,1,2-trifluoro-2-chloro-ethoxy)-pyrimidineYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

25 g of 2 -amino-4-hydroxy-6-methyl-pyrimidine, 25.6 g of chlorotrifluoroethylene, 13.8 of potassium hydroxide and 200 ml of dimethylformamide are stirred together at 60° in an autoclave for 8 hours. The mixture is diluted with water and extracted with ethyl acetate and the extract is evaporated to give a dark oil. A little methylene chloride is added and the crystalline precipitate formed is separated off to give 8.7 g of 2-amino-4-methyl-6-(1,1,2,-trifluoro-2-chloro-ethoxy)-pyrimidine of melting point 73°-74° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe extract is evaporated
  3. customto give a dark oil
  4. customthe crystalline precipitate formed
  5. customis separated off

Sources & evidence

ORD record
ord-59b99921aa8a4fa5b73e3f76ee7b3786
Source dataset
uspto-grants-1987_09
Patent number
US04693741

Reaction notes

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