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

HRID 2214776노트

반응식

HRID 2214776 반응식
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

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-e6089eca1d7d4c028b17352e4ead53a4
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109204B2

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