Methyl iodide → 1-Benzhydryl-3-methyl-5-phenyl-pyrimidine-2,4-dione

HRID 1486548Notes

Reaction equation

HRID 1486548 reaction equation
[CH:1]([N:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17](=[O:26])[NH:16][C:15]1=[O:27])([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.I[CH3:29]>CC#N.C1COCC1>[CH:1]([N:14]1[CH:19]=[C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:17](=[O:26])[N:16]([CH3:29])[C:15]1=[O:27])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 90017824HCID 90017824, compound

Product 1

HCID 900173941-Benzhydryl-3-methyl-5-phenyl-pyrimidine-2,4-dioneYield 43%

Reagents, catalysts & solvents 1

HCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

The title compound was obtained according to the procedure described for the synthesis of Example 16 (Step 1) starting from 1-benzhydryl-5-phenyl-pyrimidine-2,4-dione (prepared as in Example 14, Step 2) (0.37 g, 1.01 mmol); a 1:1 mixture of was dry MeCN/THF and iodomethane were used herein. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 80:20) to afford the title compound (0.16 g, 43%) as a light-red solid. 1H NMR (400 MHz, CDCl3): δ 3.46 (s, 3H), 7.19-7.24 (m, 6H), 7.28-7.43 (m, 11H). MS (ESI) m/z: 369 [m-H]+.

Workup

  1. customdescribed for the synthesis of Example 16 (Step 1)
  2. additiona 1:1 mixture
  3. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-9eeece61372c42038a7f3f2cff876302
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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