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

HRID 6850

Reaction equation

HRID 6850 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]

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 filtered washed with methanol to afford IIb-7.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe resulting slurry was filtered
  4. washwashed with methanol
  5. customto afford IIb-7

Sources & evidence

ORD record
ord-2810a450ddcc4664936267dcc3b490d2
Source dataset
uspto-grants-2006_08
Patent number
US07084159B2

Linked notes

Loading…