4-(Trifluoromethoxy)phenylboronic acid → 3-Hydroxy-1-[6-(4-trifluoromethoxy-phenyl)-pyridin-3-ylmethyl]-1H-thieno[3,2-d]pyrimidine-2,4-dione

HRID 550718Notes

Reaction equation

HRID 550718 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.[F:21][C:22]([F:34])([F:33])[O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>>[OH:19][N:11]1[C:12](=[O:18])[C:13]2[S:17][CH:16]=[CH:15][C:14]=2[N:9]([CH2:8][C:5]2[CH:6]=[N:7][C:2]([C:27]3[CH:26]=[CH:25][C:24]([O:23][C:22]([F:21])([F:33])[F:34])=[CH:29][CH:28]=3)=[CH:3][CH:4]=2)[C:10]1=[O:20]

Participants

3

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 116667261-(6-chloro-pyridin-3-ylmethyl)-3-hydroxy-1H-thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 115901753-Hydroxy-1-[6-(4-trifluoromethoxy-phenyl)-pyridin-3-ylmethyl]-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 (from previous example) and 4-trifluoromethoxy phenylboronic acid via general procedure C. The crude product was purified by mass-triggered preparative HPLC. 1H NMR (DMSO-d6) δ 10.85 (bs, 1H), 8.72 (d, 1H, J=1.8 Hz), 8.17 (d, 1H, J=8.7 Hz), 8.16 (d, 1H, J=5.5 Hz), 7.97 (d, 1H, J=8.1 Hz), 7.82 (dd-1H, J=1.8, 8.1 Hz), 7.47 (d, 2H, J=8.7 Hz), 7.45 (d, 1H, J=5.5 Hz), 5.40 (s, 2H); Electrospray MS: 436 (M+H); retention time: 2.84 min.

Workup

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

Sources & evidence

ORD record
ord-a6f0648294284f6e853d1a014eb32d05
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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