Cyclopentylamine → Cyclopentylamine

HRID 1162568Notes

Reaction equation

HRID 1162568 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[CH:9]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:14][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:14][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:7]=1.[CH:9]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

7

Reactant 3

HCID 2906CyclopentylamineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 3

HCID 2906CyclopentylamineYield 209.6%HCID 623440534-Pyrimidinamine, 2-chloro-N-cyclopentyl-HCID 86079789HCID 86079789, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-Chloro-pyrimidin-4yl)-cyclopentyl-amine and (4-chloro-pyrimidin-2yl)-cyclopentyl-amine were synthesized from 2,4 dichloropyrimidine (1.0 g, 6.7 mmol), cyclopentylamine (860 mg, 10.1 mmol) and DIEA (3.5 mL, 20.2 mmol) following procedure P, method P2, using THF as solvent. The crude products were purified by silica gel chromatography eluting with DCM/ethyl acetate (9:1) to afford 2-Chloro-pyrimidin-4-yl)-cyclopentyl-amine (598 mg). LCMS m/z: 199 (M+1)+, and (4-chloro-pyrimidin-2-yl)-cyclopentyl-amine (285 mg). LCMS m/z: 199 (M+1)+.

Workup

  1. customThe crude products were purified by silica gel chromatography
  2. washeluting with DCM/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-50b65b86bf3546b78f863688a173a652
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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