Ammonium Chloride → 4'-[(2-Methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

HRID 1673750Notes

Reaction equation

HRID 1673750 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].C[O-].[Na+].[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([C:30](=O)[CH2:31][CH2:32][CH3:33])[C:25](OCC)=[O:26])=[CH:19][CH:18]=1)#[N:10].[Cl-].[NH4+]>CO.C(OCC)(=O)C>[CH3:3][C:2]1[NH:4][C:25](=[O:26])[C:24]([CH2:23][C:20]2[CH:21]=[CH:22][C:17]([C:12]3[C:11]([C:9]#[N:10])=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:18][CH:19]=2)=[C:30]([CH2:31][CH2:32][CH3:33])[N:5]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 67170Acetamidine monohydrochlorideHCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 10942334Sodium Methoxide

Product 1

HCID 1354272734'-[(2-Methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of acetamidine hydrochloride (70 g) in methanol (500 ml) was added sodium methoxide (28% in methanol, 214 g) dropwise, followed by addition of a solution of ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (129 g) in methanol (500 ml) at room temperature. After being stirred at room temperature for 15 hr, ethyl acetate and saturated aqueous ammonium chloride solution were added. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were successively washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting solid was collected and washed with diisopropyl ether to give the title compound as a white solid (104 g, 82%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were successively washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solid was collected
  7. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-3743707a1e4e4a1bb02cb69d03ea0420
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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