Triethylamine → 2-Chloro-N,N-dimethylpyrimidin-4-amine

HRID 1282168

Reaction equation

HRID 1282168 reaction equation
[CH3:1][NH:2][CH3:3].C(O)C.[Cl:7][C:8]1[N:13]=[C:12](Cl)[CH:11]=[CH:10][N:9]=1.C(N(CC)CC)C>O>[Cl:7][C:8]1[N:13]=[C:12]([N:2]([CH3:3])[CH3:1])[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 22184060Dimethylamine ethanol

Product 1

HCID 959752-Chloro-N,N-dimethylpyrimidin-4-amineYield 59.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 20% dimethylamine-ethanol solution (15.4 g) of 2,4-dichloropyrimidine (3.0 g) was added triethylamine (3 ml) under ice-cooling, and the mixture was stirred for 30 min. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (100 ml). The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:1) to give the title compound (1.90 g) as white crystals, m.p.=77-79° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (100 ml)
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-a940852c62624a69ae773e7e9b6edebe
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Linked notes

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