2-(4-(6-Chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol → N-(3-(2-(6-(4-(2-Hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

HRID 2042215Notes

Reaction equation

HRID 2042215 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]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[C:6]=2[N:7]=1.Cl[C:23]1[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([N:30]2[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][OH:38])[CH2:32][CH2:31]2)[CH:24]=1>>[OH:38][CH2:37][CH2:36][N:33]1[CH2:32][CH2:31][N:30]([C:25]2[N:26]=[C:27]([CH3:29])[N:28]=[C:23]([NH:1][C:2]3[N:3]=[CH:4][C:5]4[S:10][CH:9]=[C:8]([C:11]5[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=5)[C:6]=4[N:7]=3)[CH:24]=2)[CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 144795582-(4-(6-Chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanolHCID 67120132N-(3-(2-aminothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

Product 1

HCID 67120131N-(3-(2-(6-(4-(2-Hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamideYield 53.7%

Procedure

N-(3-(2-(6-(4-(2-Hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide (18 mg, 53% yield) was prepared in the same manner as Step 10 of Example 1 using N-(3-(2-aminothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide (20 mg, 0.062 mmol) and 2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol (16 mg, 0.062 mmol).

Sources & evidence

ORD record
ord-289cc1a9fb8a4bfe85466838ff685fab
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

Loading…