1-(Bromomethyl)-2-phenylbenzene → 1-Biphenyl-2-ylmethyl-3-hydroxy-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

HRID 550727Notes

Reaction equation

HRID 550727 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].[C:28]1([C:34]2[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=2[CH2:36]Br)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[C:34]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH2:36][N:9]1[C:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[S:14][C:11]=2[C:12](=[O:13])[N:7]([OH:6])[C:8]1=[O:21]

Participants

3

Reactant 2

HCID 2633651-(Bromomethyl)-2-phenylbenzeneHCID 672009343-(2,4-Dimethoxy-benzyloxy)-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 115821061-Biphenyl-2-ylmethyl-3-hydroxy-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-phenylbenzyl bromide and subsequently deptrotected to provide the title compound as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ 5.71 (s, 2H), 7.34 (d, J=8 Hz, 1H), 7.40-7.90 (m, 12H), 8.30 (d, J=8 Hz, 1H); Ret. time=3.22 min., m/z=399.0.

Sources & evidence

ORD record
ord-e0c0b356aaba4649a70276ffbc785efb
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

Loading…