Acetic Acid → HCID 57674595, 화합물

HRID 490116

반응식

HRID 490116 반응식
[CH3:1][S:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([C:9]2[C:10]([NH2:15])=[N:11][NH:12][C:13]=2[NH2:14])[CH:4]=1.C(O[CH:19]=[C:20]([CH3:23])[CH:21]=O)C.C(O)(=[O:26])C.ClC1C=CC=C(C(OO)=O)C=1>C(O)(C)C.C(OCC)(=O)C.[OH-].[Na+]>[CH3:23][C:20]1[CH:19]=[N:14][C:13]2[N:12]([N:11]=[C:10]([NH2:15])[C:9]=2[C:5]2[CH:4]=[C:3]([S:2]([CH3:1])=[O:26])[N:8]=[CH:7][N:6]=2)[CH:21]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 70297m-Chloroperbenzoic acidHCID 5591983-Ethoxy-2-methyl-2-propenalHCID 576745294-(6-(methylthio)pyrimidin-4-yl)-1H-pyrazole-3,5-diamine

생성물 1

HCID 57674595HCID 57674595, 화합물수율 30%

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
160 °C

실험 절차

4-(6-(methylthio)pyrimidin-4-yl)-1H-pyrazole-3,5-diamine (1.0 g, 4.5 mmol) was combined with 3-ethoxy-2-methylacrylaldehyde (0.63 g, 5.3 mmol) in isopropanol (12 mL). Acetic acid (0.1 mL) was added to the reaction mixture which was then sealed in a microwave vessel and heated to 160° C. for 15 min. The reaction mixture was diluted with ethyl acetate (200 mL) and 1N NaOH (60 mL), the layers separated and the organic layer concentrated to 60 mL. This solution was cooled to 0° C. and 77% m-chloroperbenzoic acid (1.9 g, 8.5 mmol) was added. After 1 hr. a yellow precipitate formed which was filter off, washed with ethyl acetate and dried to give the product, 0.39 g, 30% yield. LCMS MH+289.29. H NMR (500 MHz, DMSO-d6) 9.02 (s, 1H) 8.91 (s, 1H), 8.88 (s, 1H), 8.54 (s, 1H), 7.14 (s, 2H), 2.91 (s, 3H), 2.34 (s, 3H).

후처리

  1. customwas then sealed in a microwave vessel
  2. customthe layers separated
  3. concentrationthe organic layer concentrated to 60 mL
  4. temperatureThis solution was cooled to 0° C.
  5. customa yellow precipitate formed which
  6. filtrationwas filter off
  7. washwashed with ethyl acetate
  8. customdried
  9. customto give the product, 0.39 g, 30% yield

출처 및 근거

ORD 기록
ord-5c8de0bb817b4576a1026089a29adc09
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528138B2

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