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

HRID 1962139Notes

Reaction equation

HRID 1962139 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-a1a127fc06f24cd9a7138796f86d8102
Source dataset
uspto-grants-2013_04
Patent number
US08415355B2

Reaction notes

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