2-(Trifluoromethyl)benzeneboronic acid → 3-Hydroxy-1-[6-(2-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-1H-thieno[3,2-d]pyrimidine-2,4-dione

HRID 550719Notes

Reaction equation

HRID 550719 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:33])([F:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O>>[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:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[C:22]([F:33])([F:32])[F:21])=[CH:3][CH:4]=2)[C:10]1=[O:20]

Participants

3

Reactant 2

HCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 116667261-(6-chloro-pyridin-3-ylmethyl)-3-hydroxy-1H-thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 115026263-Hydroxy-1-[6-(2-trifluoromethyl-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 and 2-trifluoromethyl phenylboronic acid via general procedure C. The crude product was purified by mass-triggered preparative HPLC. 1H NMR (DMSO-d6) δ 10.78 (bs, 1H), 8.68 (d, 1H, J=2.1 Hz), 8.18 (d, 1H, J=5.4 Hz), 7.85 (d, 1H, J=8.1 Hz), 7.80 (dd, 1H, J=2.1, 8.1 Hz), 7.75 (t, 1H, J=7.5 Hz), 7.66 (t, 1H, J=7.8 Hz), 7.56-7.46 (m, 3H), 5.39 (s, 2H); Electrospray MS: 420 (M+H); retention time; 2.44 min.

Workup

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

Sources & evidence

ORD record
ord-2ba9ee40f8f54161b43f4c6b40a21a65
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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