Guanidine, 1,1-dimethyl-, sulfate → 4'-{[2-(Dimethylamino)-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile

HRID 1718244Notes

Reaction equation

HRID 1718244 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][CH:10]=1)#[N:2].S(O)(O)(=O)=O.[CH3:32][N:33]([CH3:37])[C:34]([NH2:36])=[NH:35].[O-]CC.[Na+].C(O)C>C(O)C>[CH3:32][N:33]([CH3:37])[C:34]1[NH:36][C:17](=[O:18])[C:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:10][CH:11]=2)=[C:22]([CH2:23][CH2:24][CH3:25])[N:35]=1

Participants

5

Reactant 3

HCID 220673Guanidine, 1,1-dimethyl-, sulfateHCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 1360267224'-{[2-(Dimethylamino)-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrileYield 30.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (6.41 g) and N,N-dimethylguanidine sulfate (5.0 g) in ethanol (100 mL) was added 20% sodium ethoxide-ethanol solution (11 mL), and the mixture was heated under reflux for 24 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was washed with water and diethyl ether to give the title compound (2.06 g, 30%) as a pale-yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. customthe solvent was evaporated under reduced pressure
  4. washThe residue was washed with water and diethyl ether

Sources & evidence

ORD record
ord-64adc89b027543a0bf32664d7f0e7099
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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