Acetic Acid → 2-(methylthio)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidine

HRID 2214776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2214776
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=1)=O.[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C>C(O)C>[CH3:14][S:13][C:9]1[N:8]=[C:7]([C:5]2[N:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:2]=[CH:3][CH:4]=2)[CH:12]=[CH:11][N:10]=1.[CH3:14][S:13][C:9]1[N:8]=[C:7]([C:5]2[CH:4]=[CH:3][N:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:23]=2)[CH:12]=[CH:11][N:10]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 7516PhenylhydrazineHCID 21948442(E)-3-(dimethylamino)-1-(2-(methylthio)pyrimidin-4-yl)prop-2-en-1-one

Produkt 2

HCID 219485112-(methylthio)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidineHCID 219485342-(methylthio)-4-(1-phenyl-1H-pyrazol-3-yl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of (2E)-3-(dimethylamino)-1-[2-(methylthio)pyrimidin-4-yl]prop-2-en-1-one (1-4, 3.60 g, 16.1 mmol, 1 equiv), phenylhydrazine (1.58 mL, 16.1 mmol, 1.00 equiv) and acetic acid (90 uL, 1.6 mmol, 0.10 equiv) in ethanol (100 mL) was heated at reflux for 20 hours. The reaction mixture was concentrated and the residue purified by flash column chromatography (hexanes initially, grading to 40% ethyl acetate in hexanes) to give 2-(methylthio)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidine (1-5) and 2-(methylthio)-4-(1-phenyl-1H-pyrazol-3-yl)pyrimidine (1-6) as white solids. 1H NMR 1–5 (300 MHz, CDCl3) δ 8.44 (d, 1H, J=5.2 Hz), 7.77 (d, 1H, J=1.8 Hz), 7.50–7.30 (m, 5H), 6.95 (d, 1H, J=1.8 Hz), 6.92 (d, 1H, J=5.2 Hz), 2.08 (s, 3H); 1H NMR 1–6 (300 MHz, CDCl3) δ 8.60 (d, 1H, J=4.9 Hz), 8.02 (d, 1H), J=1.8 Hz), 6.92 (d, 1H, J=4.9 Hz), 7.68 (br d, 2H, j=7.8 Hz), 7.52 (br t, 2H, J=7.5 Hz), 7.37 (m, 1H), 7.23 (d, 1H, J=1.8 Hz), 2.68 (s, 3H).

Aufarbeitung

  1. temperatureat reflux for 20 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue purified by flash column chromatography (hexanes initially

Quellen und Nachweise

ORD-Eintrag
ord-e6089eca1d7d4c028b17352e4ead53a4
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109204B2

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