3,3-Dimethyl-1-butenylboronic acid → 1-[6-(3,3-Dimethyl-but-1-enyl)-pyridin-3-ylmethyl]-3-hydroxy-1H-thieno[3,2-d]pyrimidine-2,4-dione

HRID 550720Notes

Reaction equation

HRID 550720 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[C:12](=[O:18])[N:11]([OH:19])[C:10]2=[O:20])=[CH:4][CH:3]=1.[C:21]([CH:25]=[CH:26]B(O)O)([CH3:24])([CH3:23])[CH3:22]>>[CH3:22][C:21]([CH3:24])([CH3:23])[CH:25]=[CH:26][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[C:12](=[O:18])[N:11]([OH:19])[C:10]2=[O:20])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27632983,3-Dimethyl-1-butenylboronic acidHCID 116667261-(6-chloro-pyridin-3-ylmethyl)-3-hydroxy-1H-thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 672031691-[6-(3,3-Dimethyl-but-1-enyl)-pyridin-3-ylmethyl]-3-hydroxy-1H-thieno[3,2-d]pyrimidine-2,4-dione

Procedure

The title compound was prepared from 1-(6-chloro-pyridin-3-ylmethyl)-3-hydroxy-1H-thieno[3,2-d]pyrimidine-2,4-dione and 2-tert-butyl vinyl boronic acid via general procedure C. The crude product was purified by mass-triggered preparative HPLC. 1H NMR (DMSO-d6) δ 10.8 (bs, 1H), 8.53 (d, 1H, J=2.1 Hz), 8.14 (d, 1H, J=5.4 Hz), 7.62 (dd, 1H, J=2.1, 7.8 Hz), 7.38 (d, 1H, J=5.1 Hz), 7.36 (d, 1H, J=7.8 Hz), 6.78 (d, 1H, J=16.2 Hz), 6.35 (d, 1H, J=16.2 Hz), 5.29 (s, 2H), 1.09 (s, 9H); Electrospray MS: 358 (M+H); retention time: 2.62 min.

Workup

  1. customThe crude product was purified by mass-triggered preparative HPLC

Sources & evidence

ORD record
ord-5968eb5aca834b92af452ccce89490a4
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

Loading…