Benzyl Bromide → 1-Benzyl-3-hydroxy-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

HRID 550723Notes

Reaction equation

HRID 550723 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].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([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])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 672009343-(2,4-Dimethoxy-benzyloxy)-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 116527331-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 benzyl bromide and subsequently deprotected to provide the title compound as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ 5.75 (s, 2H); 7.20-7.45 (m, 6H); 7.56 (ddd, J1=8 Hz, J2=1 Hz, 1H); 7.93 (d, J=9 Hz, 1H); 8.15 (d, J=8 Hz, 1H); 11.06 (br s, 1H); retention time=2.57 min., m/z=325.0.

Sources & evidence

ORD record
ord-c070b60ee65a42fea50a7532c91cfe0c
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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