Cyclopentylamine → 5-Bromo-2-chloro-N-cyclopentyl-4-pyrimidinamine

HRID 1853187Notes

Reaction equation

HRID 1853187 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:10]1([NH2:15])[CH2:14][CH2:13][CH2:12][CH2:11]1.CCN(C(C)C)C(C)C>CCO>[Br:1][C:2]1[C:3]([NH:15][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 442482475-Bromo-2-chloro-N-cyclopentyl-4-pyrimidinamineYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a large sealed tube is added 5-bromo-2,4-dichloropyrimidine (3 g, 13.2 mmol) in 100 mL of EtOH. Then cyclopentyl amine (1.95 mL, 19.75 mmol) and N,N′-diisopropylethylamine (3.36 mL, 19.8 mmol) are added to the solution at rt. The solution is then stirred rt overnight. Solvent is evaporated and the crude is purified using silica gel chromatography (15% ethyl acetate/85% hexane) to give (5-bromo-2-chloro-pyrimidin-4-yl)-cyclopentyl-amine as a white solid (3.25 g, 89%). MS (ESI) m/z 278.4 (M+H)+

Workup

  1. customSolvent is evaporated
  2. customthe crude is purified

Sources & evidence

ORD record
ord-e3de2e464fb74995847911ca9dcd74cb
Source dataset
uspto-grants-2015_02
Patent number
US08962630B2

Reaction notes

Loading…