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

HRID 2359566Notes

Reaction equation

HRID 2359566 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-81bffe00ffc54f5897eb058c1df797ae
Source dataset
uspto-grants-2014_04
Patent number
US08685980B2

Reaction notes

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