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

HRID 2222245Notes

Reaction equation

HRID 2222245 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]>C1COCC1>[Br:1][C:2]1[C:3]([NH:11][CH3:10])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 107277715-bromo-2-chloro-N-methylpyrimidin-4-amineYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

5-Bromo-2,4-dichloro-pyrimidine (2.41 g, 10.6 mmol) is slowly treated with methylamine (8 M in EtOH, 3.3 mL) in THF (15 mL) at about −20° C. After stirring for 30 minutes at about −20° C., the reaction mixture is partitioned between CHCl3 and saturated NaHCO3. The aqueous layer is extracted with additional CHCl3 twice and the combined organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography (SiO2, EtOAc/Hexane=3/7) to give 1.76 g (75%) of (5-bromo-2-chloro-pyrimidin-4-yl)-methylamine as a white solid.

Workup

  1. customthe reaction mixture is partitioned between CHCl3 and saturated NaHCO3
  2. extractionThe aqueous layer is extracted with additional CHCl3 twice
  3. dry with materialthe combined organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by column chromatography (SiO2, EtOAc/Hexane=3/7)

Sources & evidence

ORD record
ord-a435d97d10b74d0d93978be0ac94c0f1
Source dataset
uspto-grants-2008_05
Patent number
US07371750B2

Reaction notes

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