Carbamimidic acid, methyl ester, sulfate (1:1) → 4'-[(2-Methoxy-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

HRID 1718241Notes

Reaction equation

HRID 1718241 reaction equation
S(O)(O)(=O)=O.[C:6](=[NH:10])([O:8][CH3:9])[NH2:7].C[O-].[Na+].[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29]([C:35](=O)[CH2:36][CH2:37][CH3:38])[C:30](OCC)=[O:31])=[CH:24][CH:23]=1)#[N:15]>CO>[CH3:9][O:8][C:6]1[NH:7][C:30](=[O:31])[C:29]([CH2:28][C:25]2[CH:26]=[CH:27][C:22]([C:17]3[C:16]([C:14]#[N:15])=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:23][CH:24]=2)=[C:35]([CH2:36][CH2:37][CH3:38])[N:10]=1

Participants

5

Reactant 3

HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 10942334Sodium Methoxide

Product 1

HCID 1360267204'-[(2-Methoxy-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrileYield 16.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl imidocarbamate sulfate (10 g), 28% sodium methoxide (26 mL) and ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (15.8 g) in methanol (100 mL) was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and water and acetic acid were added. The precipitated solid was collected by filtration, washed with water and diethyl ether to give the title compound (2.62 g, 16%) as a colorless solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and acetic acid
  2. additionwere added
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-7c690fa062bb4221902b4ae712358eeb
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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