Sodium Methoxide → 4'-[(2-Ethyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

HRID 1673810Notes

Reaction equation

HRID 1673810 reaction equation
Cl.[C:2](=[NH:6])([NH2:5])[CH2:3][CH3:4].C[O-].[Na+].[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([C:30](=O)[CH2:31][CH2:32][CH3:33])[C:26](OC)=[O:27])=[CH:20][CH:19]=1)#[N:11]>CO>[CH2:3]([C:2]1[NH:6][C:26](=[O:27])[C:25]([CH2:24][C:21]2[CH:22]=[CH:23][C:18]([C:13]3[C:12]([C:10]#[N:11])=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:19][CH:20]=2)=[C:30]([CH2:31][CH2:32][CH3:33])[N:5]=1)[CH3:4]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12301253Propionimidamide hydrochlorideHCID 57460349HCID 57460349, compound

Product 1

HCID 1354305644'-[(2-Ethyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of propanimidamide hydrochloride (20 g), 28% sodium methoxide (56 mL) and methyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (34 g) in methanol (350 mL) was stirred overnight. The solvent was evaporated under reduced pressure, and water and 1 M hydrochloric acid were added. The precipitated solid was collected by filtration, and washed with water and diethyl ether to give the title compound (27 g, 82%) as a pale-yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and 1 M hydrochloric acid
  2. additionwere added
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-c3db3a9d838842b4992d4edd21c9d7ca
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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