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Sodium Methoxide → 4'-[(4-Butyl-2-ethyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]-3'-fluorobiphenyl-2-carbonitrile

HRID 1718462
Notes
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Reaction equation

HRID 1718462 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][CH2:33][CH3:34])[C:26](OC)=[O:27])=[C:20]([F:36])[CH:19]=1)#[N:11]>CO>[CH2:31]([C:30]1[N:6]=[C:2]([CH2:3][CH3:4])[NH:5][C:26](=[O:27])[C:25]=1[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[C:12]([C:10]#[N:11])=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:19][C:20]=1[F:36])[CH2:32][CH2:33][CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12301253Propionimidamide hydrochlorideHCID 57460325Methyl 2-[(2'-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxoheptanoate

Product 1

HCID 1360269094'-[(4-Butyl-2-ethyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]-3'-fluorobiphenyl-2-carbonitrileYield 53%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

A solution of propanimidamide hydrochloride (7.5 g), 28% sodium methoxide (23 mL) and methyl 2-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxoheptanoate (8.4 g) in methanol (84 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 (4.7 g, 53%) 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-94a289b6b9e945a2b7132394ea706292
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07803940B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes