4-(Trifluoromethyl)phenylboronic acid → 1-Benzhydryl-5-[4-(trifluoromethyl)phenyl]pyrimidine-2,4-dione

HRID 1486543Notes

Reaction equation

HRID 1486543 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.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>>[CH:1]([N:14]1[CH:19]=[C:18]([C:28]2[CH:29]=[CH:30][C:25]([C:24]([F:35])([F:34])[F:23])=[CH:26][CH:27]=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 27343894-(Trifluoromethyl)phenylboronic acidHCID 716549651-Benzhydryl-5-iodo-pyrimidine-2,4-dione

Product 1

HCID 900177931-Benzhydryl-5-[4-(trifluoromethyl)phenyl]pyrimidine-2,4-dioneYield 45%

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 (0.33 g, 0.82 mmol) and 4-(trifluoromethyl)phenylboronic acid (0.23 g, 1.22 mmol). The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 70:30) to afford the title compound (0.15 g, 45%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 6.99 (s, 1H), 7.27-7.33 (m, 4H), 7.35-7.46 (m, 6H), 7.47 (s, 1H), 7.55-7.63 (m, 2H), 7.65-7.73 (m, 2H), 11.78 (s, 1H). MS (ESI) m/z: 371 [M-H]−. MS (ESI) m/z: 373 [M-H]+, 390 [M-NH4]+.

Workup

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

Sources & evidence

ORD record
ord-4b9f6b1d6e1c44f5966b67de03b2fb31
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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