4-(3-Dimethylamino-acryloyl)-3,4-dimethyl-5-methylsulfanyl-4,5-dihydro-thiophene-2-carbonitrile → 3-Methyl-5-methylsulfanyl-4-(2-phenylamino-pyrimidin-4-yl)-thiophene-2-carbonitrile

HRID 478179Notes

Reaction equation

HRID 478179 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1(C)[CH:11]([S:12][CH3:13])[S:10][C:9]([C:14]#[N:15])=[C:8]1[CH3:16])=O.[C:19]1([NH:25][C:26]([NH2:28])=[NH:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C.CO>[CH3:16][C:8]1[C:7]([C:5]2[CH:4]=[CH:3][N:28]=[C:26]([NH:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:27]=2)=[C:11]([S:12][CH3:13])[S:10][C:9]=1[C:14]#[N:15]

Participants

5

Reactant 2

HCID 738591674-(3-Dimethylamino-acryloyl)-3,4-dimethyl-5-methylsulfanyl-4,5-dihydro-thiophene-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

4-(3-Dimethylamino-acryloyl)-3,4-dimethyl-5-methylsulfanyl-4,5-dihydro-thiophene-2-carbonitrile (0.2 mmol) was combined with N-phenyl-guanidine (0.2 mmol) in acetonitrile (0.25 mL) and the resulting mixture heated at reflux for 24 hours. The reaction mixture was diluted with methanol (3mL) and the resulting slurry filtered and the solid was washed with methanol (2 mL) then dried under nitrogen to afford IIa-37. M+H=507.1, HPLC: Rt=6.196 minutes, 1H NMR (500 Mz, DMSO) 9.77(s, 1H), 8.25(d, 1H, J=5.3 Hz), 7.69(s, 1H), 7.48(m, 2H), 7.48(m, 4H), 7.41(t, 2H, J=7.3 Hz), 7.34(t, 1H, J=7.2 Hz), 7.25(d, 1H, J=8.3 Hz), 7.21 (t, 1H, J=8.0 Hz), 6.67(d, 1H, J=6.7 Hz), 6.01(d, 1H, J=5.3 Hz), 5.11(s, 2H), 3.32(s, 3H, CH3), 2.68(s, 3H, CH3).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 24 hours
  3. filtrationthe resulting slurry filtered
  4. washthe solid was washed with methanol (2 mL)
  5. customthen dried under nitrogen
  6. customto afford IIa-37

Sources & evidence

ORD record
ord-c72376904a0d4344a70041b5956a0480
Source dataset
uspto-grants-2003_11
Patent number
US06642227B2

Reaction notes

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