Methylamine → 6-chloro-N-methylpyrimidin-4-amine

HRID 220087Notes

Reaction equation

HRID 220087 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][NH2:10]>C(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:10][CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 709434,6-Dichloropyrimidine

Product 1

HCID 3094796-chloro-N-methylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,6-dichloro-pyrimidine(3.53 g, 23.7 mmol) and methylamine (33 wt % in ethanol, 10 ml, 80 mmol) in ethanol is kept stirring overnight at room temperature. The reaction mixture is concentrated, triturated with water and filtered. The crude product is washed with water, a small amount of ethanol and ethyl ether sequentially, and air-dried to give (6-Chloro-pyrimidin-4-yl)-methyl-amine as white powder: 1H NMR 400 MHz (d6-DMSO) δ 8.36-8.16 (m, 1H), 7.69 (s, 1H), 6.50 (s, 1H), 2.90-2.68 (m, 3H); MS m/z 144.00 (M+1).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customtriturated with water
  3. filtrationfiltered
  4. washThe crude product is washed with water
  5. dry with materiala small amount of ethanol and ethyl ether sequentially, and air-dried

Sources & evidence

ORD record
ord-4144f76f29b84f228abb86521a858161
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Reaction notes

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