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

HRID 1673796
Notes
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Reaction equation

HRID 1673796 reaction equation
Cl.[CH:2]1([CH2:5][C:6](=[NH:8])[NH2:7])[CH2:4][CH2:3]1.C[O-].[Na+].[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27]([C:32](=O)[CH2:33][CH2:34][CH2:35][CH3:36])[C:28](OC)=[O:29])=[CH:22][CH:21]=1)#[N:13]>CO>[CH2:33]([C:32]1[N:8]=[C:6]([CH2:5][CH:2]2[CH2:4][CH2:3]2)[NH:7][C:28](=[O:29])[C:27]=1[CH2:26][C:23]1[CH:22]=[CH:21][C:20]([C:15]2[C:14]([C:12]#[N:13])=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:25][CH:24]=1)[CH2:34][CH2:35][CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10807723Methyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoateHCID 10942334Sodium MethoxideHCID 574603332-Cyclopropylethanimidamide hydrochloride

Product 1

HCID 1360269144'-{[4-Butyl-2-(cyclopropylmethyl)-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

A solution of 2-cyclopropylethanimidamide hydrochloride (3.9 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 (4.3 g, 76%) 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-f0eb8d13bcf7479b88f742193cdf9204
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07998968B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes