Triethylamine → 4-(4-chlorobenzyl)-1-(7H-pyrrolo(2,3-d)pyrimidin-4-yl)piperidin-4-amine

HRID 1470264Notes

Reaction equation

HRID 1470264 reaction equation
Cl.[Cl:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][C:8]2([NH2:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.Cl[C:18]1[C:19]2[CH:26]=[CH:25][NH:24][C:20]=2[N:21]=[CH:22][N:23]=1.C(N(CC)CC)C>C(O)CCC>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2([NH2:14])[CH2:9][CH2:10][N:11]([C:18]3[C:19]4[CH:26]=[CH:25][NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[CH2:12][CH2:13]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 668730314-(4-Chlorobenzyl)-piperidin-4-ylamine hydrochloride

Product 1

HCID 177518194-(4-chlorobenzyl)-1-(7H-pyrrolo(2,3-d)pyrimidin-4-yl)piperidin-4-amineYield 49.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-(4-chlorobenzyl)piperidin-4-yl amine hydrochloride (0.060 g, 0.2016 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.031 g, 0.2016 mmol) and triethylamine (0.140 ml, 1.0079 mmol) in n-butanol (2.0 ml) was heated to 100° C. for 24 hours. Concentration and purification by preparative silica TLC gave a white solid (0.034 g, 49%). LC-MS (LCT) m/z 342 [M+H+], Rt 3.25 min.

Workup

  1. concentrationConcentration and purification by preparative silica TLC

Sources & evidence

ORD record
ord-3c0502448eaa4803b67d2c6b19350e21
Source dataset
uspto-grants-2015_04
Patent number
US09006430B2

Reaction notes

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