Methyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoate → 4'-[(4-Butyl-6-oxo-2-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

HRID 1673793Notes

Reaction equation

HRID 1673793 reaction equation
Cl.[C:2](=[NH:7])([NH2:6])[CH2:3][CH2:4][CH3:5].C[O-].[Na+].[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([C:31](=O)[CH2:32][CH2:33][CH2:34][CH3:35])[C:27](OC)=[O:28])=[CH:21][CH:20]=1)#[N:12]>CO>[CH2:32]([C:31]1[N:7]=[C:2]([CH2:3][CH2:4][CH3:5])[NH:6][C:27](=[O:28])[C:26]=1[CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:14]2[C:13]([C:11]#[N:12])=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:24][CH:23]=1)[CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 10807723Methyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoateHCID 10942334Sodium MethoxideHCID 12828983Butanimidamide hydrochloride

Product 1

HCID 1360269124'-[(4-Butyl-6-oxo-2-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of butanimidamide hydrochloride (3.5 g), 28% sodium methoxide (8.7 mL) and methyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoate (5.0 g) in methanol (50 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 (4.5 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-1b7eca6ec8144b28840962bf78ee222b
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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