Potassium Carbonate → 4'-[(2-ethoxy-4-methyl-6-oxopyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrile

HRID 1673621Notes

Reaction equation

[CH2:1]([O:3][C:4]1[NH:9][C:8](=[O:10])[CH:7]=[C:6]([CH3:11])[N:5]=1)[CH3:2].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4]1[N:9]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:18][CH:19]=2)[C:8](=[O:10])[CH:7]=[C:6]([CH3:11])[N:5]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-ethoxy-6-methylpyrimidin-4(3H)-one (4.9 g) and 4′-(bromomethyl)biphenyl-2-carbonitrile (10.3 g) in acetonitrile (120 mL) was added potassium carbonate (5.24 g), and the mixture was stirred at 50° C. for 12 hr. The insoluble material was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography to give the title compound (6.15 g, 56%) as a colorless solid.

Workup

filtrationThe insoluble material was filtered off
concentrationthe filtrate was concentrated
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-47d35edb769948d39e73f4904e63deab
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998968B2

Reaction notes

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