Tolylboronic acid → 1-Benzhydryl-5-(p-tolyl)pyrimidine-2,4-dione

HRID 1486542Notes

Reaction equation

[CH:1]([N:14]1[CH:19]=[C:18](I)[C:17](=[O:21])[NH:16][C:15]1=[O:22])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(O)(O)[C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1>>[CH:1]([N:14]1[CH:19]=[C:18]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:17](=[O:21])[NH:16][C:15]1=[O:22])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 79799Tolylboronic acid

HCID 716549651-Benzhydryl-5-iodo-pyrimidine-2,4-dione

Product 1

HCID 900168691-Benzhydryl-5-(p-tolyl)pyrimidine-2,4-dioneYield 50.3%

Procedure

The title compound was obtained according to the procedure: described for the synthesis of Example 14 (Step 2), starting from 1-benzhydryl-5-iodo-pyrimidine-2,4-dione (0.11 g, 0.27 mmol) and p-tolylboronic acid (0.06 g, 0.41 mmol). The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 75:25) to afford the title compound (0.05 g, 50%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.32 (s, 3H), 7.11-7.15 (m, 3H), 7.20-7.24 (m, 6H), 7.34-7.44 (m, 6H), 8.16 (s, 1H). MS (ESI) m/z: 369 [M-H]−.

Workup

customdescribed for the synthesis of Example 14 (Step 2)
customThe crude was purified by column chromatography

Sources & evidence

ORD record: ord-e11bfb6792094cb083409792ef780732
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428465B2

Reaction notes

Loading…