Potassium Carbonate → N-cyclopropyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine

HRID 729341ノート

反応式

HRID 729341 の反応式
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[N:9][N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[N:11]2)=O.[CH:17]1([NH:20][C:21]([NH2:23])=[NH:22])[CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:17]1([NH:20][C:21]2[N:23]=[C:5]([C:7]3[CH:8]=[N:9][N:10]4[C:15]=3[CH:14]=[CH:13][CH:12]=[N:11]4)[CH:4]=[CH:3][N:22]=2)[CH2:19][CH2:18]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11458585HCID 11458585、化合物HCID 178512453HCID 178512453、化合物

生成物 1

HCID 6918710N-cyclopropyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine収率 75%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
165 °C

実験手順

To a solution of (2E)-3-(dimethylamino)-1-pyrazolo[1,5-b]pyridazin-3-yl-2-propen-1-one (43 mg, 0.20 mmol) in DMF (2 mL) was added N-cyclopropylguanidine.0.5H2SO4 (160 mg, 0.80 mmol) and potassium carbonate (110 mg, 0.80 mmol). The reaction was heated at an oil bath temperature of 165° C. for about 18 hours. The mixture was cooled to RT and the solvent was removed in vacuo. The residue was dissolved in chloroform and filtered. The filtrate was purified by flash column chromatography (0-10% gradient MeOH/CH2Cl2) to give the title compound as a yellow solid (38 mg, 75%). 1H-NMR (400 MHz, d6-DMSO) δ 9.13 (dd, 1H, J=9.0, 1.6 Hz), 8.77 (s, 1H), 8.53 (dd, 1H, J=4.4, 1.6 Hz), 8.24 (d, 1H, J=5.2 Hz), 7.38 (m, 1H), 7.10 (d, 1H, J=5.2 Hz), 2.72 (m, 1H), 0.71 (m, 2H), 0.47 (m, 2H); MS (ESI) (M+H)+ 253.

後処理

  1. temperatureThe mixture was cooled to RT
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. filtrationfiltered
  5. customThe filtrate was purified by flash column chromatography (0-10% gradient MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-b23a439e47614ba9a6cc1f5c5cee315f
出典データセット
uspto-grants-2009_09
特許番号
US07582630B2

反応ノート

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