Ethyl Acetoacetate → HCID 178429161、化合物

HRID 472850

反応式

HRID 472850 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([NH2:13])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.O=[C:15]([CH3:22])[CH2:16][C:17](OCC)=[O:18]>CC1C=CC=CC=1C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]3[N:13]=[C:15]([CH3:22])[CH:16]=[C:17]([OH:18])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 8868Ethyl AcetoacetateHCID 1785072813-(3-chlorophenyl)-1H-pyrazol-5-amine

生成物 1

HCID 178429161HCID 178429161、化合物収率 88%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
157.5 °C

実験手順

A suspension of 3-(3-chlorophenyl)-1H-pyrazol-5-amine (10 g, 51.6 mmol) and ethyl 3-oxobutanoate (26.3 ml, 207 mmol) in o-xylene (200 mL) was heated at reflux (oil bath temp: 155-160° C.) for 20 h. Note: The reaction turned clear solution between 60-70° C. and solids started crashing out at 130° C. Then, cooled, diluted with hexanes (100 mL), filtered, washed with hexanes (100 mL) and dried to afford 2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-7-ol (11.8 g, 45.4 mmol, 88% yield) as off-white solid. 1H NMR (400 MHz, DMSO-d6) δ: 12.46 (s, 1H), 8.05 (s, 1H), 8.00-7.95 (m, 1H), 7.56-7.45 (m, 2H), 6.70 (s, 1H), 5.64 (s, 1H), 2.33 (s, 3H). LCMS (M+H) calcd for C13H11ClN6O: 260.06. found: 260.1.

後処理

  1. temperaturewas heated
  2. custombetween 60-70° C.
  3. customstarted crashing out at 130° C
  4. temperatureThen, cooled
  5. filtrationfiltered
  6. washwashed with hexanes (100 mL)
  7. customdried

出典と根拠

ORDレコード
ord-9878c0973b224a8ba36dec8bb73a6da1
出典データセット
uspto-grants-2014_01
特許番号
US08633200B2

関連ノート

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