Water → (6-Chloro-pyrimidin-4-yl)-[3-(4-methyl-piperazin-1-yl)-propyl]-amine

HRID 58154

Reaction equation

HRID 58154 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][NH2:28])[CH2:21][CH2:20]1.O>CC(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:28][CH2:27][CH2:26][CH2:25][N:22]2[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 709434,6-DichloropyrimidineHCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 118024570(6-Chloro-pyrimidin-4-yl)-[3-(4-methyl-piperazin-1-yl)-propyl]-amineYield 51.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4,6-dichloro-pyrimidine (1.5 g, 10 mmol) and DIPEA (1.55 g, 12 mmol) in iPrOH (50 mL) was added a solution of 3-(4-methyl-piperazin-1-yl)-propylamine (1.73 g, 11 mmol) at room temperature. The resulting mixture was stirred at room temperature for 2 hours. Water was added and the mixture was extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated to afford the title compound (1.4 g, 51%), which was used directly in the next step without further purification. MS (ESI): 270 [M+H]+.

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f2185db81fe14e08b1f93afe3b2633b1
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

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