Triethylamine → 885499-63-8

HRID 1470267Notes

Reaction equation

HRID 1470267 reaction equation
Cl.[Cl:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][C:8]2([CH2:14][NH2:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.Cl[C:19]1[C:20]2[CH:27]=[CH:26][NH:25][C:21]=2[N:22]=[CH:23][N:24]=1.C(N(CC)CC)C>C(O)CCC>[Cl:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][C:8]2([CH2:14][NH2:15])[CH2:13][CH2:12][N:11]([C:19]3[C:20]4[CH:27]=[CH:26][NH:25][C:21]=4[N:22]=[CH:23][N:24]=3)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 66873182885500-40-3

Product 1

HCID 11696113885499-63-8Yield 56%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of C-[4-(4-chlorobenzyl)piperidin-4-yl]methyl amine hydrochloride (0.063 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 SCX-2 Isolute column (2 g), eluting with 1M NH3/MeOH, followed by silica column chromatography (15% methanol in DCM) gave a white solid (0.040 g, 56%). LC-MS (LCT2) m/z 356 [M+H+], Rt 2.97 min.

Workup

  1. concentrationConcentration and purification by SCX-2 Isolute column (2 g)
  2. washeluting with 1M NH3/MeOH

Sources & evidence

ORD record
ord-62384a1b886a4f94b7edbabba3e87f9b
Source dataset
uspto-grants-2015_04
Patent number
US09006430B2

Reaction notes

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