Methyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate → HCID 178503357, compound

HRID 624816

Reaction equation

HRID 624816 reaction equation
C[O:2][C:3](=O)[C:4]([C:10]#[N:11])=[C:5](SC)[S:6][CH3:7].[NH2:13][C:14]1[CH:18]=[CH:17][NH:16][N:15]=1>C(O)C>[OH:2][C:3]1[N:15]2[N:16]=[CH:17][CH:18]=[C:14]2[N:13]=[C:5]([S:6][CH3:7])[C:4]=1[C:10]#[N:11]

Participants

4

Reactant 2

HCID 319957Methyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoateHCID 178418806HCID 178418806, compound

Product 1

HCID 178503357HCID 178503357, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under nitrogen gas atmosphere, 2-cyano-3,3-bismethylthio-2-propenoic methyl ester (6 g, 29.5 mmol) was added to ethanol (40 mL) along with 3-aminopyrazole (2.6 g, 31 mmol) and the mixture was refluxed for 2.5 hours. The reaction was then cooled to room temperature and precipitate was collected by filtration under vacuum. The solid was washed with ethanol and dried under vacuum to give 7-hydroxy-5-(methylthio)pyrazolo[1,5-a]pyrimidine-6-carbonitrile in 67% yield (4.1 g). This material was used for the next step without further purification. LCMS (M+1=207)

Workup

  1. temperaturethe mixture was refluxed for 2.5 hours
  2. filtrationprecipitate was collected by filtration under vacuum
  3. washThe solid was washed with ethanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-42f1683331804e74b76cc2792bba2865
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Linked notes

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