2-(4-(6-Chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol → N-Cyclopropyl-3-(2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thieno[3,2-d]pyrimidin-7-yl)benzamide

HRID 2042223Notes

Reaction equation

HRID 2042223 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[C:13]([CH:20]=[CH:21][CH:22]=3)[C:14]([NH:16][CH:17]3[CH2:19][CH2:18]3)=[O:15])[C:6]=2[N:7]=1.Cl[C:24]1[N:29]=[C:28]([CH3:30])[N:27]=[C:26]([N:31]2[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][OH:39])[CH2:33][CH2:32]2)[CH:25]=1>>[CH:17]1([NH:16][C:14](=[O:15])[C:13]2[CH:20]=[CH:21][CH:22]=[C:11]([C:8]3[C:6]4[N:7]=[C:2]([NH:1][C:24]5[CH:25]=[C:26]([N:31]6[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][OH:39])[CH2:33][CH2:32]6)[N:27]=[C:28]([CH3:30])[N:29]=5)[N:3]=[CH:4][C:5]=4[S:10][CH:9]=3)[CH:12]=2)[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 144795582-(4-(6-Chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanolHCID 671201443-(2-aminothieno[3,2-d]pyrimidin-7-yl)-N-cyclopropylbenzamide

Product 1

HCID 52931895N-Cyclopropyl-3-(2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thieno[3,2-d]pyrimidin-7-yl)benzamideYield 47.1%

Procedure

N-Cyclopropyl-3-(2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thieno[3,2-d]pyrimidin-7-yl)benzamide (16 mg, 47% yield) was prepared in the same manner as Step 10 of Example 1 using 3-(2-aminothieno[3,2-d]pyrimidin-7-yl)-N-cyclopropylbenzamide (20 mg, 0.064 mmol) and 2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol (17 mg, 0.064 mmol).

Sources & evidence

ORD record
ord-14a5f28c3fa14b77a9a3dc11bcc7b89a
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

Loading…