(2H-1,3-benzodioxol-5-yl)boronic acid → HCID 11560977, compound

HRID 550746Notes

Reaction equation

HRID 550746 reaction equation
Br[C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:10]2[C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[O:13][C:9]=2[C:8](=[O:18])[N:7]([OH:19])[C:6]1=[O:20].[CH2:25]1[O:33][C:32]2[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][C:27]=2[O:26]1>>[O:26]1[C:27]2[CH:28]=[CH:29][C:30]([C:24]3[CH:2]=[C:3]([CH:21]=[CH:22][CH:23]=3)[CH2:4][N:5]3[C:10]4[C:11]5[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=5[O:13][C:9]=4[C:8](=[O:18])[N:7]([OH:19])[C:6]3=[O:20])=[CH:31][C:32]=2[O:33][CH2:25]1

Participants

3

Reactant 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 11552793HCID 11552793, compound

Product 1

HCID 11560977HCID 11560977, compound

Procedure

1-(2-Bromo-benzyl)-3-hydroxy-1H-benzo[4,5]furo[3,2-d]pyrimidine-2,4-dione was treated with 3,4-methylenedioxyphenylboronic acid according to general procedure C to provide the title compound as a yellow solid. 1H NMR (d6-DMSO, 300 MHz) 5.61 (s, 2H); 6.05 (s, 2H); 6.98 (d, J=8 Hz, 1H); 7.10 (dd, J1=8 Hz, J2=2 Hz, 1H); 7.18-7.21 (m, 2H); 7.35 (dd, J=8 Hz, 2H); 7.49 (br d, J=8 Hz, 1H); 7.57-7.62 (m, 2H); 7.80 (d, J=8 Hz, 1H); 7.87 (d, J=8 Hz, 1H); Ret. time=2.95 min., m/z=429.0.

Sources & evidence

ORD record
ord-c10d85392ef94d679424f5d9c009e6e9
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

Loading…