4-Chloro-6-(ethylamino)pyrimidine → N-Methyl-N'-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-pyrimidine-4,6-diamine

HRID 1038737Notes

Reaction equation

HRID 1038737 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]([NH:25][CH2:26]C)[CH:20]=1>>[CH3:26][NH:25][C:21]1[CH:20]=[C:19]([NH:17][C:14]2[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:12][CH:13]=2)[N:24]=[CH:23][N:22]=1

Participants

3

Reactant 2

HCID 5884524-Chloro-6-(ethylamino)pyrimidineHCID 230087924-[2-(4-Methylpiperazin-1-yl)ethoxy]aniline

Product 1

HCID 66670033N-Methyl-N'-{4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenyl}-pyrimidine-4,6-diamine

Conditions

Temperature
150 °C

Procedure

The title compound is prepared as described in Example 160A but using 4-[2-(4-methyl-piperazin-1-yl)-ethoxy]-phenylamine (500 mg, 2.13 mmol, 1 eq.), (6-chloro-pyrimidin-4-yl)-ethyl-amine and stirring the reaction mixture at 150° C. for 20 h. Purification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1) followed by trituration in diethyl ether affords 250 mg of the title compound as a white solid: ESI-MS: 343.2 [MH]+; tR=1.00 min (gradient J); TLC: Rf=0.23 (DCM/MeOH+1% NH3aq, 9:1).

Workup

  1. customThe title compound is prepared
  2. customPurification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1)

Sources & evidence

ORD record
ord-25535164f18b4fd3a43056e012f01167
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

Loading…