4-Fluorobenzyl bromide → 4-(2-chloro-9-(4-fluorobenzyl)-9H-purin-6-yl)morpholine

HRID 2093423Notes

Reaction equation

HRID 2093423 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:3]=1.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[N:3]=1

Participants

3

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 32746034-(2-chloro-9H-purin-6-yl)morpholine

Product 1

HCID 580152274-(2-chloro-9-(4-fluorobenzyl)-9H-purin-6-yl)morpholine

Procedure

4-(2-Chloro-9H-purin-6-yl)morpholine (75 mg) was reacted with 1-(bromomethyl)-4-fluorobenzene via General Procedure C to give 4-(2-chloro-9-(4-fluorobenzyl)-9H-purin-6-yl)morpholine which was reacted with 150 mg tert-butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl carbonate via General Procedure A and purified via reverse phase HPLC to give 50 mg of 142 as a white solid. MS (Q1) 406.2 (M)+.

Sources & evidence

ORD record
ord-30ebc9880d7a4f87a917823cf581622f
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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