2-Methoxypyrimidine-5-boronic acid → 4-(2-(2-methoxypyrimidin-5-yl)-9-methyl-8-((4-(methylsulfonyl)piperazin-1-yl)methyl)-9H-purin-6-yl)morpholine

HRID 1692687Notes

Reaction equation

HRID 1692687 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]3)[N:8]2[CH3:11])=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:3]=1.[CH3:29][O:30][C:31]1[N:36]=[CH:35][C:34](B(O)O)=[CH:33][N:32]=1>>[CH3:29][O:30][C:31]1[N:36]=[CH:35][C:34]([C:2]2[N:10]=[C:9]3[C:5]([N:6]=[C:7]([CH2:12][N:13]4[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]4)[N:8]3[CH3:11])=[C:4]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:3]=2)=[CH:33][N:32]=1

Participants

3

Reactant 2

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 866372424-(2-Chloro-9-methyl-8-((4-(methylsulfonyl)piperazin-1-yl)methyl)-9H-purin-6-yl)morpholine

Product 1

HCID 445438754-(2-(2-methoxypyrimidin-5-yl)-9-methyl-8-((4-(methylsulfonyl)piperazin-1-yl)methyl)-9H-purin-6-yl)morpholine

Procedure

4-(2-Chloro-9-methyl-8-((4-(methylsulfonyl)piperazin-1-yl)methyl)-9H-purin-6-yl)morpholine (50 mg) was reacted with 2-methoxypyrimidin-5-ylboronic acid via General Procedure A and purified via reverse phase HPLC to give 5.5 mg 136 as a white solid. MS (Q1) 504.3 (M)+.

Workup

  1. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-65cc69722f1942498c89cc23b66e2f9e
Source dataset
uspto-grants-2012_04
Patent number
US08158624B2

Reaction notes

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