5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → 2-(2-(6-aminopyridin-3-yl)-9-methyl-6-morpholino-9H-purin-8-yl)propan-2-ol

HRID 2093410Notes

Reaction equation

HRID 2093410 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:12]([OH:15])([CH3:14])[CH3:13])[N:8]2[CH3:11])=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:3]=1.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=2)O1>>[NH2:36][C:33]1[N:34]=[CH:35][C:30]([C:2]2[N:10]=[C:9]3[C:5]([N:6]=[C:7]([C:12]([OH:15])([CH3:14])[CH3:13])[N:8]3[CH3:11])=[C:4]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:3]=2)=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 580152132-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)propan-2-ol

Product 1

HCID 445437682-(2-(6-aminopyridin-3-yl)-9-methyl-6-morpholino-9H-purin-8-yl)propan-2-ol

Procedure

2-(2-Chloro-9-methyl-6-morpholino-9H-purin-8-yl)propan-2-ol (95 mg) was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine via Procedure A and purified via reverse phase HPLC to give 89.3 mg of 131 as a white solid. MS (Q1) 370.3 (M)+

Workup

  1. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-3614431e5acd4d828fb8d6d62bebc42d
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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