3-Pyridinylboronic acid → 1-Benzhydryl-5-(3-pyridyl)pyrimidine-2,4-dione

HRID 1486553Notes

Reaction equation

HRID 1486553 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.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=1>>[CH:1]([N:14]1[CH:19]=[C:18]([C:25]2[CH:24]=[N:23][CH:28]=[CH:27][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 27343783-Pyridinylboronic acidHCID 716549651-Benzhydryl-5-iodo-pyrimidine-2,4-dione

Product 1

HCID 900184521-Benzhydryl-5-(3-pyridyl)pyrimidine-2,4-dioneYield 24%

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 (0.81 g, 2 mmol) and 3-pyridylboronic acid (0.370 g, 3 mmol). The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 30:70) to afford the title compound (0.17 g, 24%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.14 (s, 1H), 7.20-7.24 (m, 4H), 7.29-7.33 (m, 2H), 7.36-7.46 (m, 6H), 7.93 (dt, J=8.1, 2.0 Hz, 1H), 8.41 (d, J=1.7 Hz, 1H), 8.45 (s, 1H), 8.52 (dd, J=4.9, 1.6 Hz, 1H). MS (ESI) m/z: 356 [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-f40bfba67ca74a22bb3eb81fb67a5586
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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