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

HRID 1673572Notes

Reaction equation

HRID 1673572 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-cec00dc8a2544bb3902ae653a9d67419
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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