4-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amine → 2-(2-(2-amino-4-methylpyrimidin-5-yl)-9-(2-hydroxyethyl)-6-morpholino-9H-purin-8-yl)propan-2-ol

HRID 2093387Notes

Reaction equation

HRID 2093387 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:15]([C:16]([OH:19])([CH3:18])[CH3:17])=[N:14][C:13]2[C:8]1=[N:9][C:10](Cl)=[N:11][C:12]=2[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)(=O)C.[CH3:27][C:28]1[C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][N:31]=[C:30]([NH2:43])[N:29]=1>>[NH2:43][C:30]1[N:29]=[C:28]([CH3:27])[C:33]([C:10]2[N:9]=[C:8]3[C:13]([N:14]=[C:15]([C:16]([OH:19])([CH3:17])[CH3:18])[N:7]3[CH2:6][CH2:5][OH:4])=[C:12]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:11]=2)=[CH:32][N:31]=1

Participants

3

Reactant 2

HCID 529879064-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amineHCID 580152242-(2-Chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)ethyl acetate

Product 1

HCID 445449432-(2-(2-amino-4-methylpyrimidin-5-yl)-9-(2-hydroxyethyl)-6-morpholino-9H-purin-8-yl)propan-2-ol

Procedure

2-(2-Chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)ethyl acetate (300 mg) was treated with 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine via General Procedure A and was purified via reverse phase HPLC to give 107 mg of 102 as a white solid. MS (Q1) 415.2 (M)+

Workup

  1. customwas purified via reverse phase HPLC

Sources & evidence

ORD record
ord-b64237db46104d908ff913ce4ae49030
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

Loading…