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

HRID 2214776ノート

反応式

HRID 2214776 の反応式
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

参加物

6

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-e6089eca1d7d4c028b17352e4ead53a4
出典データセット
uspto-grants-2006_09
特許番号
US07109204B2

反応ノート

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