Methylamine → 4-Chloro-6-(methylamino)pyrimidine-5-carbaldehyde

HRID 907431Notes

Reaction equation

HRID 907431 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[CH3:11][NH2:12]>C1COCC1>[Cl:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([NH:12][CH3:11])[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Product 1

HCID 122782664-Chloro-6-(methylamino)pyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-dichloro-pyrimidine-5-carbaldehyde Compound 2a (0.5 g), methylamine (88 mg) and THF (50 mL) were added to a flask. The mixture was stirred at rt overnight, then concentrated and the residue was purified by flash chromatography (silica gel, hexane:EtOAc/5:5) to afford 4-chloro-6-methylamino-pyrimidine-5-carbaldehyde Compound 2b (0.40 g, 82%). 1H NMR (300 MHz, CDCl3) δ 10.38 (s, 1H), 9.15 (s, 1H), 8.45 (s, 1H), 3.15 (d, 3 H). MS (ESI) m/z: 172 (M+H+).

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by flash chromatography (silica gel, hexane:EtOAc/5:5)

Sources & evidence

ORD record
ord-8642c296f126406d9ee9df53e76b3591
Source dataset
uspto-grants-2011_09
Patent number
US08013153B2

Reaction notes

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