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

HRID 1673611
Notes
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Reaction equation

HRID 1673611 reaction equation
[CH2:1]([C:5]1[NH:10][C:9](=[O:11])[CH:8]=[C:7]([CH:12]2[CH2:14][CH2:13]2)[N:6]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]([C:29]#[N:30])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([C:5]1[N:10]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[C:24]([C:29]#[N:30])=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:21][CH:22]=2)[C:9](=[O:11])[CH:8]=[C:7]([CH:12]2[CH2:14][CH2:13]2)[N:6]=1)[CH2:2][CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 1360267532-butyl-6-cyclopropylpyrimidin-4(3H)-one

Product 1

HCID 574600894'-[(2-butyl-4-cyclopropyl-6-oxopyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrileYield 44%

Reagents, catalysts & solvents 1

HCID 6342Acetonitrile
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-butyl-6-cyclopropylpyrimidin-4(3H)-one (6 g) and 4′-(bromomethyl)biphenyl-2-carbonitrile (9.34 g) in acetonitrile (180 mL) was added potassium carbonate (8.63 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 (5.23 g, 44%) as a colorless viscous substance.

Workup

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

Sources & evidence

ORD record
ord-03ae88cb89aa4342a8bc9a8062614735
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07998968B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes