Phenylboronic Acid → 1-Biphenyl-3-ylmethyl-3-hydroxy-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

HRID 550733Notes

Reaction equation

HRID 550733 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][N:6]1[C:11]2[C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[S:14][C:10]=2[C:9](=[O:19])[N:8]([OH:20])[C:7]1=[O:21].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[C:2]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:24]=[CH:23][CH:22]=[C:4]([CH2:5][N:6]2[C:11]3[C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[S:14][C:10]=3[C:9](=[O:19])[N:8]([OH:20])[C:7]2=[O:21])[CH:3]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 116828241-(3-Bromo-benzyl)-3-hydroxy-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 115314281-Biphenyl-3-ylmethyl-3-hydroxy-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione

Procedure

1-(3-Bromo-benzyl)-3-hydroxy-1H-benzo[4,5]thieno[3,2-d]pyrimidine-2,4-dione was treated with phenylboronic acid according to general procedure C. The title compound was obtained as a yellow solid following purification by preparative HPLC. 1H NMR (d6-DMSO, 300 MHz) δ 5.79 (s, 2H); 7.26-7.69 (m, 10H); 8.00 (d, J=9 Hz, 1H); 8.13 (d, J=8 Hz, 2H); Ret. time=3.19 min., m/z=399.0.

Sources & evidence

ORD record
ord-a51efa6b92394377b95696b8b10e39c8
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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