1-(2-Bromoethyl)-2-chlorobenzene → HCID 178492623, compound

HRID 736638Notes

Reaction equation

HRID 736638 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][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31]>>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][CH2:23][N:15]1[C:14]2[C:19]([N:20]=[C:12]([S:11][C:4]3[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N:13]=2)=[C:18]([NH2:21])[N:17]=[CH:16]1

Participants

3

Reactant 2

HCID 27569631-(2-Bromoethyl)-2-chlorobenzeneHCID 178492621HCID 178492621, compound

Product 1

HCID 178492623HCID 178492623, compound

Procedure

The title compounds were prepared from 8-(2,5-dimethoxy-phenylsulfanyl)-9H-purin-6-ylamine and 1-(2-bromo-ethyl)-2-chloro-benzene by a procedure similar to examples 1 and 2. The isomers were separated by preparative HPLC. 9-[2-(2-Chloro-phenyl)-ethyl]-8-(2,5-dimethoxy-phenylsulfanyl)-9H-purin-6-ylamine: Yield 18%, 1H NMR (DMSO-d6) δ 8.23 (s, 1H), 7.82 (bs, 2H), 7.36 (dd, J=8.0, 1.2 Hz, 1H), 7.24-7.15 (m, 2H), 7.03-6.99 (m, 2H), 6.85 (dd, J=9.2, 3.2 Hz, 1H), 6.47 (d, J=2.8 Hz, 1H), 4.46 (t, J=7.2 Hz, 2H), 3.73 (s, 3H), 3.61 (s, 3H), 3.16 (t, J=7.2 Hz, 2H); LC-MS [M+H]+ 442.1. 3-[2-(2-Chloro-phenyl)-ethyl]-8-(2,5-dimethoxy-phenylsulfanyl)-3H-purin-6-ylamine: Yield, 11%, 1H NMR (DMSO-d6) δ 8.34 (s, 1H), 8.16 (bs, 1H), 7.41 (m, 1H), 7.29-7.11 (m, 6H), 4.56 (t, J=6.8 Hz, 2H), 3.76 (s, 3H), 3.72 (s, 3H), 3.30 (t, J=6.8 Hz, 2H), LC-MS [M+H]+ 442.1.

Workup

  1. customThe isomers were separated by preparative HPLC

Sources & evidence

ORD record
ord-3e0d8666aec14d96a60897e15c242f91
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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