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Acetamidine monohydrochloride → 2'-Methoxy-4'-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

HRID 1718922
Notes
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Reaction equation

HRID 1718922 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([C:22](=O)[CH2:23][CH2:24][CH3:25])[C:17](OCC)=[O:18])=[CH:11][C:10]=1[O:27][CH3:28])#[N:2].Cl.[C:30](=[NH:33])([NH2:32])[CH3:31].C[O-].[Na+]>CO>[CH3:28][O:27][C:10]1[CH:11]=[C:12]([CH2:15][C:16]2[C:17](=[O:18])[NH:32][C:30]([CH3:31])=[N:33][C:22]=2[CH2:23][CH2:24][CH3:25])[CH:13]=[CH:14][C:9]=1[C:4]1[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 57460898Ethyl 2-[(2'-cyano-2-methoxybiphenyl-4-yl)methyl]-3-oxohexanoate

Product 1

HCID 1361468682'-Methoxy-4'-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrileYield 52%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To a suspension of 60% sodium hydride (1.80 g) in tetrahydrofuran (50 mL) was added dropwise a solution of ethyl butyrylacetate (9.50 g) in tetrahydrofuran (30 mL). After stirring for 30 min, 4′-(bromomethyl)-2′-methoxybiphenyl-2-carbonitrile (8.79 g) was added. The mixture was stirred at room temperature for 15 hr, and 1 M hydrochloric acid was added. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to give ethyl 2-[(2′-cyano-2-methoxybiphenyl-4-yl)methyl]-3-oxohexanoate. Then, a solution of the obtained ethyl 2-[(2′-cyano-2-methoxybiphenyl-4-yl)methyl]-3-oxohexanoate, ethanimidamide hydrochloride (3.25 g) and 28% sodium methoxide (9.91 g) in methanol (70 mL) was stirred overnight. The solvent was evaporated under reduced pressure, and saturated aqueous ammonium chloride solution was added to the residue. The precipitated solid was collected by filtration, and washed with water and diethyl ether to give the title compound (5.63 g, 52%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and saturated aqueous ammonium chloride solution
  2. additionwas added to the residue
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-ca2ca6c0efe244e1a0a34535bed54e48
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07803940B2

Reaction notes

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