Phenethyl bromide → 3-Hydroxy-1-phenethyl-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

HRID 550729Notes

Reaction equation

HRID 550729 reaction equation
COC1C=C(OC)C=CC=1C[O:6][N:7]1[C:12](=[O:13])[C:11]2[S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:10]=2[NH:9][C:8]1=[O:21].Br[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[OH:6][N:7]1[C:12](=[O:13])[C:11]2[S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:10]=2[N:9]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:8]1=[O:21]

Participants

3

Reactant 2

HCID 7666Phenethyl bromideHCID 672009343-(2,4-Dimethoxy-benzyloxy)-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 117028143-Hydroxy-1-phenethyl-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

Procedure

Following general procedure B2 and D1, 3-(2,4-Dimethoxy-benzyloxy)-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione was alkylated with 2-Bromoethylbenzene and subsequently deprotected to provide the title compound as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ 3.08-3.14 (m, 2H); 4.67-4.73 (m, 2H); 7.24-7.38 (m, 5H); 7.61-7.69 (m, 2H); 8.20 (dd, J1=7 Hz, J2=2 Hz, 1H); 8.30 (dd, J1=7 Hz, J2=2 Hz, 1H); Ret. time=2.77 min., m/z=339.0.

Sources & evidence

ORD record
ord-e6d73e6c96a442a7ba9a8384a3883561
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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