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Sodium hydride → 3-(4-phenoxyphenyl)-1-(tetrahydropyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

HRID 432159
ノート
印刷プレビュー

反応式

HRID 432159 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[NH:16][N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].S(C1C=CC(C)=CC=1)(O[CH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)(=O)=O>CC(N(C)C)=O>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[N:16]([CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 13961807Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonateHCID 178508717HCID 178508717、化合物2 回

生成物 1

HCID 223468363-(4-phenoxyphenyl)-1-(tetrahydropyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine収率 18%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
105 °C

実験手順

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (Compound 15) (0.97 g) in 33 mL dry dimethylacetamide was stirred under nitrogen while adding 60% sodium hydride (0.22 g). After 30 minutes tetrahydropyran-4-yl tosylate (1.0 g) was added and the mixture heated at 105° C. for 4 hours then 135° C. for 3.5 hours. Evaporation in vacuo and treating with water gave pale brown solid which was collected and washed well with water then dried in air. Flash chromatography in 19:1 ethyl acetate:triethylamine afforded 0.22 g (18%) of 3-(4-phenoxyphenyl)-1-(tetrahydropyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine m.p. 187-187.5° C. Calculated for C22H21N5O2 C 68.2H 5.4 N 18.1 Found C 68.1H 5.5 N 18.0.

後処理

  1. customEvaporation in vacuo
  2. additiontreating with water
  3. customgave pale brown solid which
  4. customwas collected
  5. washwashed well with water
  6. customthen dried in air

出典と根拠

ORDレコード
ord-e01c64f90d554cc7bb2e0fc7eccf9072
出典データセット
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06660744B1

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート