3-Pyridinylboronic acid → 4-(9-methyl-8-((4-(methylsulfonyl)piperazin-1-yl)methyl)-2-(pyridin-3-yl)-9H-purin-6-yl)morpholine

HRID 1692688Notes

Reaction equation

HRID 1692688 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.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31](B(O)O)[CH:30]=1>>[CH3:11][N:8]1[C:7]([CH2:12][N:13]2[CH2:14][CH2:15][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:17][CH2:18]2)=[N:6][C:5]2[C:9]1=[N:10][C:2]([C:31]1[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=1)=[N:3][C:4]=2[N:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 866372424-(2-Chloro-9-methyl-8-((4-(methylsulfonyl)piperazin-1-yl)methyl)-9H-purin-6-yl)morpholine

Product 1

HCID 445438744-(9-methyl-8-((4-(methylsulfonyl)piperazin-1-yl)methyl)-2-(pyridin-3-yl)-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 pyridin-3-ylboronic acid via General Procedure A and purified via reverse phase HPLC to give 33.4 mg 137 as a white solid. MS (Q1) 473.3 (M)+

Workup

  1. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-24266da934a944a7a71c715e7b744d2b
Source dataset
uspto-grants-2012_04
Patent number
US08158624B2

Reaction notes

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