Dimethylamine, hydrochloride → 2-Amino-4-chloromethyl-6-dimethylaminopyrimidine

HRID 3910

Reaction equation

HRID 3910 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[Na].[NH2:6][C:7]1[N:12]=[C:11](Cl)[CH:10]=[C:9]([CH2:14][Cl:15])[N:8]=1>CO>[NH2:6][C:7]1[N:8]=[C:9]([CH2:14][Cl:15])[CH:10]=[C:11]([N:3]([CH3:4])[CH3:2])[N:12]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 5360545SodiumHCID 201534884-Chloro-6-(chloromethyl)pyrimidin-2-amine

Product 1

HCID 201535022-Amino-4-chloromethyl-6-dimethylaminopyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

8.1 Parts of dimethylamine hydrochloride was added to a solution of 2.3 parts of sodium in 20 parts of methanol. The resulting mixture was added dropwise with stirring over about 10 minutes to a solution of 9.9 parts of 2-amino-4-chloro-6-chloromethylpyrimidine in 50 parts of methanol. The reaction was monitored by TLC and when reaction was complete the solvent was evaporated and the residue stirred with about 20 parts of water. The solid obtained was filtered and dried. The product was purified by chromatography on silica, eluted with ethyl acetate, followed by sublimation at 110° C./0.04 mb to give 2-amino-4-chloromethyl-6-dimethylaminopyrimidine m.p. 127°-129° C.

Workup

  1. additionThe resulting mixture was added dropwise
  2. customThe reaction was monitored by TLC and when reaction
  3. customwas evaporated
  4. customThe solid obtained
  5. filtrationwas filtered
  6. customdried
  7. customThe product was purified by chromatography on silica
  8. washeluted with ethyl acetate
  9. customfollowed by sublimation at 110° C.

Sources & evidence

ORD record
ord-49bd71cf48ae45fcbb90a9526cdec8dd
Source dataset
uspto-grants-1988_02
Patent number
US04723006

Linked notes

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