Hydrochloric Acid → 3-(3-Methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 239623ノート

反応式

HRID 239623 の反応式
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C=O)C.C(O)C.O.ClCCl>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH2:11])[NH:4][N:3]=2)[CH:17]=[CH:16][CH:15]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 178508725HCID 178508725、化合物

生成物 1

HCID 1784899393-(3-Methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine収率 27%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.522 g, 2.0 mmoles) in DMF (10 ml), ethanol (5 ml) and water (5 ml), 3-methoxyphenylboronic acid (0.395 g, 2.59 mmoles) and sodium carbonate (1.05 g, 10 mmoles) were added and the system is degassed for 30 min. Palladium tetrakis triphenylphosphine (0.455 g, 0.39 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture neutralised with 1.5N HCl, extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as off-white solid (0.130 g, 27% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 13.57(s, 1H), 8.20(s, 1H), 7.46(t, J=7.8 Hz, 1H), 7.23(d, J=7.5 Hz, 1H), 7.18(d, J=2.4 Hz, 1H), 7.04 (dd, J=8.0,1.8 Hz, 1H), 3.81(s, 3H).

後処理

  1. customthe system is degassed for 30 min
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography with methanol

出典と根拠

ORDレコード
ord-e746d06849cc4d2ab0c149710bc26e47
出典データセット
uspto-grants-2014_02
特許番号
US08642607B2

反応ノート

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