4-Nitrobenzyl bromide → HCID 24895931, compound

HRID 736642Notes

Reaction equation

HRID 736642 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[S:11][C:12]1[NH:13][C:14]2[C:19]([N:20]=1)=[C:18]([NH2:21])[N:17]=[CH:16][N:15]=2.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[S:11][C:12]1[N:13]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:14]2[C:19]([N:20]=1)=[C:18]([NH2:21])[N:17]=[CH:16][N:15]=2

Participants

3

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 178492621HCID 178492621, compound

Product 1

HCID 24895931HCID 24895931, compoundYield 10%

Procedure

The title compound was prepared from 8-(2,5-dimethoxy-phenylsulfanyl)-9H-purin-6-ylamine and 1-bromomethyl-4-nitro-benzene by a procedure similar to examples 1 and 2. The compound was purified by preparative HPLC. 8-(2,5-Dimethoxy-phenylsulfanyl)-9-(4-nitro-benzyl)-9H-purin-6-ylamine: Yield 10%, 1H NMR (DMSO-d6) δ 8.20 (s, 1H), 8.04 (d, J=6.8 Hz, 2H), 7.57 (bs, 2H), 7.30 (d, 6.8 Hz, 2H), 6.88 (d, J=8.4 Hz, 1H), 6.70 (dd, J=9.2, 3.2 Hz, 1H), 6.25 (d, J=2.8 Hz, 1H), 5.52 (s, 2H), 3.71 (s, 3H), 3.52 (s, 3H); LC-MS [M+H]+ 439.1.

Workup

  1. customThe compound was purified by preparative HPLC

Sources & evidence

ORD record
ord-2fc74404bb0d410e8905ca430ade5c8d
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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