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4-(3-Dimethylamino-acryloyl)-3-methyl-5-methylsulfanylthiophene-2-carbonitrile → 3-Methyl-5-methylsulfanyl-4-(2-phenylamino-pyrimidin-4-yl)-thiophene-2-carbonitrile

HRID 478182
Notes
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Reaction equation

HRID 478182 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:8]([CH3:16])=[C:9]([C:14]#[N:15])[S:10][C:11]=1[S:12][CH3:13])=O.[C:18]1([NH:24][C:25]([NH2:27])=[NH:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C.CO>[CH3:16][C:8]1[C:7]([C:5]2[CH:4]=[CH:3][N:27]=[C:25]([NH:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:26]=2)=[C:11]([S:12][CH3:13])[S:10][C:9]=1[C:14]#[N:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 5360484-(3-Dimethylamino-acryloyl)-3-methyl-5-methylsulfanylthiophene-2-carbonitrileHCID 178418923HCID 178418923, compound

Product 1

HCID 101319583-Methyl-5-methylsulfanyl-4-(2-phenylamino-pyrimidin-4-yl)-thiophene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(3-dimethylamino-acryloyl)-3-methyl-5-methylsulfanyl-thiophene-2-carbonitrile (0.2 mmol) in acetonitrile (0.25 mL) was added N-phenyl guanidine (1 equivalent, 0.2 mmol) and the reaction heated at reflux for 24 hours. The resulting mixture was cooled to room temperature then diluted with methanol (3 mL). The resulting slurry was filterred washed with methanol to afford IIb-7.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 24 hours
  3. washThe resulting slurry was filterred washed with methanol
  4. customto afford IIb-7

Sources & evidence

ORD record
ord-73e9ced857cf41be983ffb5d132e590c
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06642227B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes