Methylamine → 2,5-dichloro-N-methylpyrimidin-4-amine

HRID 1503294Notes

Reaction equation

HRID 1503294 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[CH3:10][NH2:11]>CO>[Cl:1][C:2]1[N:7]=[C:6]([NH:11][CH3:10])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 189812472,5-dichloro-N-methylpyrimidin-4-amineYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a cooled (0° C.) solution of 2,4,5-trichloropyrimidine (2.0 g, 11 mmol) in methanol (30 mL) was added dropwise a 2 M solution of methylamine in methanol (6.3 mL). The reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated and redissolved in DCM. The solution was washed with sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (0-40% EtOAc in heptane) to give 2,5-dichloro-N-methylpyrimidin-4-amine (0.9 g, 50%). 1H-NMR (DMSO): δ 8.13 (s, 1H), 7.89 (s, 1H), 2.86 (d, J=4.5, 3H).

Workup

  1. concentrationThe reaction was then concentrated
  2. dissolutionredissolved in DCM
  3. washThe solution was washed with sat. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (0-40% EtOAc in heptane)

Sources & evidence

ORD record
ord-622ad1055fe1431982bee4d940f0ebd9
Source dataset
uspto-grants-2015_12
Patent number
US09212173B2

Reaction notes

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