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

HRID 58126Notes

Reaction equation

HRID 58126 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][NH2:10].C1COCC1.CCOC(C)=O>CC(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:10][CH3:9])[CH:7]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 709434,6-Dichloropyrimidine

Product 1

HCID 3094796-chloro-N-methylpyrimidin-4-amineYield 62%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4,6-dichloro-pyrimidine (7.45 g, 50 mmol) in iPrOH (50 mL) was added a solution of methyl amine in THF (2M, 30 mL, 60 mmol) at room temperature. The resulting mixture was stirred for 18 hours. The mixture was concentrated and the residue was purified by flash chromatography on silica eluting with DCM:EtOAc=6:1-1:1 to obtain the title compound (4.4 g, yield: 62%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.96 (d, 3H), 5.22-5.36 (bs, 1H), 6.35 (s, 1H), 8.35 (s, 11H); MS (ESI): 144 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography on silica eluting with DCM

Sources & evidence

ORD record
ord-be2f740bdb93431cbfa5a50b841b792a
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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