Acetic Acid → HCID 57674595、化合物

HRID 490116

反応式

HRID 490116 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 57674595HCID 57674595、化合物収率 30%

試薬・触媒・溶媒 3

HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5c8de0bb817b4576a1026089a29adc09
出典データセット
uspto-grants-2009_05
特許番号
US07528138B2

関連ノート

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