4-Amino-6-chloropyrimidine → N-{4-[2-(4-Methyl-piperazin-1-yl)-ethoxy]-phenyl}-pyrimidine-4,6-diamine

HRID 1038725Notes

Reaction equation

HRID 1038725 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.Cl[C:19]1[N:24]=[CH:23][N:22]=[C:21]([NH2:25])[CH:20]=1>O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:19]3[CH:20]=[C:21]([NH2:25])[N:22]=[CH:23][N:24]=3)=[CH:13][CH:12]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 2380124-Amino-6-chloropyrimidineHCID 230087924-[2-(4-Methylpiperazin-1-yl)ethoxy]aniline

Product 1

HCID 66670025N-{4-[2-(4-Methyl-piperazin-1-yl)-ethoxy]-phenyl}-pyrimidine-4,6-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

The title compound is prepared as described in Example 152A but using 4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenylamine (300 mg, 1.28 mmol, 1 eq.), 6-chloro-pyrimidin-4-ylamine, water (0.5 ml), and stirring the reaction mixture for 2 h at 150° C. The crude product is purified by trituration in diethyl ether to afford the title compound as a white solid. ESI-MS: 329.1 [MH]+; tR=0.98 min (purity: 100%, gradient J).

Workup

  1. customThe title compound is prepared
  2. customThe crude product is purified by trituration in diethyl ether

Sources & evidence

ORD record
ord-fbc2a8f4fba64da1b09f6f55cec92761
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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