Cinnamyl chloride → 3-Hydroxy-1-(3-phenyl-allyl)-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

HRID 550730Notes

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](Cl)/[CH:29]=[CH: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]([CH2:28][CH:29]=[CH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:8]1=[O:21]

Participants

Reactant 2

HCID 639658Cinnamyl chloride

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

Product 1

HCID 672017283-Hydroxy-1-(3-phenyl-allyl)-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 trans-cinnamyl chloride and subsequently deprotected to provide the title compound as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ 5.24 (s, 1H); 5.25 (s, 1H); 6.51-6.67 (m, 2H); 7.21 (dd, J=7 Hz, 1H); 7.28 (dd, J=8 Hz, 2H); 7.40 (d, J=7 Hz, 2H); 7.53 (dd, J=8 Hz, 1H); 7.61 (dd, J=8 Hz, 1H); 8.16 (d, J=8 Hz, 1H); 8.25 (d, J=8 Hz, 1H), 11.00 (br s, 1H); Ret. time=2.79 min., m/z=350.0.

Sources & evidence

ORD record: ord-f51c05cfc8804783af7a3bc8c5ada9d5
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947691B2

Reaction notes

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