(3-Bromopropyl)benzene → HCID 178493614, compound

HRID 736640Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:13][C:14]2[NH:15][C:16]3[C:21]([N:22]=2)=[C:20]([NH2:23])[N:19]=[CH:18][N:17]=3)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Br[CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[C:28]1([CH2:27][CH2:26][CH2:25][N:17]2[C:16]3[C:21]([N:22]=[C:14]([S:13][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=4)[N:15]=3)=[C:20]([NH2:23])[N:19]=[CH:18]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Reactant 2

HCID 12503(3-Bromopropyl)benzene

HCID 178493613HCID 178493613, compound

Product 1

HCID 178493614HCID 178493614, compound

Procedure

The title compounds were prepared from 8-(3,4,5-trimethoxy-phenylsulfanyl)-9H-purin-6-ylamine and (3-bromo-propyl)-benzene by a procedure similar to examples 1 and 2. The isomers were separated by preparative HPLC. 9-(3-Phenyl-propyl)-8-(3,4,5-trimethoxy-phenylsulfanyl)-9H-purin-6-ylamine: Yield 34%, 1H NMR (DMSO-d6) δ 8.30 (s, 1H), 7.26-7.22 (m, 2H), 7.16 (tt, J=7.6, 1.2 Hz, 1H), 7.12-7.10 (m, 2H), 6.78 (s, 2H), 4.24 (t, J=7.2 Hz, 2H), 3.72 (s, 6H), 3.63 (s, 3H), 2.56 (t, J=7.6 Hz, 2H), 1.94 (tt, J=7.6, 7.2 Hz, 2H); LC-MS [M+H]+ 452.0. 3-(3-Phenyl-propyl)-8-(3,4,5-trimethoxy-phenylsulfanyl)-3H-purin-6-ylamine: Yield, 13%, 1H NMR (DMSO-d6) δ 8.61 (s, 1H), 7.27-7.23 (m, 2H), 7.18-7.15 (m, 3H), 7.06 (s, 2H), 4.35 (t, J=7.2 Hz, 2H), 3.77 (s, 6H), 3.71 (s, 3H) 2.64 (t, J=7.2 Hz, 2H), 2.20 (quintet, J=7.2 Hz, 2H); LC-MS [M+H]+ 452.0.

Workup

customThe isomers were separated by preparative HPLC

Sources & evidence

ORD record: ord-5ec04bdaa1794f36b131369882c35c65
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595401B2

Reaction notes

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