Methylamine → 5-bromo-2-chloro-N-methylpyrimidin-4-amine

HRID 2409087Notes

Reaction equation

HRID 2409087 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][NH2:11]>CO.C(O)C>[Br:1][C:2]1[C:3]([NH:11][CH3:10])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 107277715-bromo-2-chloro-N-methylpyrimidin-4-amineYield 39%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a cooled (0° C.) solution of 5-bromo-2,4-dichloropyrimidine (5.0 g, 22 mmol) in methanol (42 mL) was added dropwise a 33 wt % solution of methylamine in ethanol (3.3 mL). The reaction was allowed to warm to room temperature. The reaction was then concentrated. The crude product was purified by column chromatography (0-10% methanol in DCM) to give 5-bromo-2-chloro-N-methylpyrimidin-4-amine (1.8 g, 39%). 1H-NMR (DMSO): δ 8.22 (s, 1H), 7.75 (s, 1H), 2.85 (d, J=3.9, 3H).

Workup

  1. concentrationThe reaction was then concentrated
  2. customThe crude product was purified by column chromatography (0-10% methanol in DCM)

Sources & evidence

ORD record
ord-f78c7c2890e34d268dbbd30eb9626f14
Source dataset
uspto-grants-2014_08
Patent number
US08815882B2

Reaction notes

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