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

Participants

Role	Name	HCID	Charge
Reactant	4-(Trifluoromethoxy)phenylboronic acid	HCID 2734386	—
Reactant	1-(6-chloro-pyridin-3-ylmethyl)-3-hydroxy-1H-thieno[3,2-d]pyrimidine-2,4-dione	HCID 11666726	—
Product	3-Hydroxy-1-[6-(4-trifluoromethoxy-phenyl)-pyridin-3-ylmethyl]-1H-thieno[3,2-d]pyrimidine-2,4-dione	HCID 11590175	—

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07947691B2
Source dataset	uspto-grants-2011_05
ORD ID	ord-a6f0648294284f6e853d1a014eb32d05
Source note	uspto-grants-2011_05