(Naphthalen-2-yl)boronic acid → 1-Benzhydryl-5-(2-naphthyl)pyrimidine-2,4-dione

HRID 1486544Notes

Reaction equation

HRID 1486544 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.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1B(O)O>>[CH:1]([N:14]1[CH:19]=[C:18]([C:25]2[CH:24]=[CH:23][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=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

3

Reactant 2

HCID 2734375(Naphthalen-2-yl)boronic acidHCID 716549651-Benzhydryl-5-iodo-pyrimidine-2,4-dione

Product 1

HCID 900176411-Benzhydryl-5-(2-naphthyl)pyrimidine-2,4-dioneYield 82.4%

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 2-naphthylboronic acid (0.07 g, 0.41 mmol). The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 70:30) to afford the title compound (0.09 g, 80%) as an off-white solid. 1H NMR (400 MHz, CDCl3): 7.17 (s, 1H), 7.24-7.27 (m, 2H), 7.36 (s, 1H), 7.38-7.47 (m, 10H), 7.76-7.88 (m, 5H), 8.28 for s, 1H). MS (ESI) m/z: 405 [M-H]+.

Workup

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

Sources & evidence

ORD record
ord-3a7826879c62477ca4e21c3d61895c49
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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