3-Bromobenzyl bromide → 1-(3-Bromo-benzyl)-3-hydroxy-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

HRID 550726Notes

Reaction equation

HRID 550726 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:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br>>[Br:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32][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 699793-Bromobenzyl bromideHCID 672009343-(2,4-Dimethoxy-benzyloxy)-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 116828241-(3-Bromo-benzyl)-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 3-bromobenzyl bromide and subsequently deprotected to provide the title compound as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ 7.10-7.18 (m, 2H); 7.22 (ddd, J1=8 Hz, J2=1 Hz, 1H); 7.31 (ddd, J1=7 Hz, J2=2 Hz, 1H); 7.39 (dd, J=8 Hz, 1H); 7.44 (s, 1H); 7.71 (d, J=8 Hz, 1H); 7.97 (d, J1=8 Hz, 1H); Ret. time=2.82 min., m/z=403.0.

Sources & evidence

ORD record
ord-6296eeecf4114077ad3abdafeae81da5
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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