Sodium hydride → 6-Amino-7-(4-fluorobenzyl)-2-[3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-7,9-dihydro-8H-purin-8-one

HRID 510107ノート

反応式

HRID 510107 の反応式
[NH2:1][C:2]1[C:7]([N:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:9](=O)[O:10]C)=[C:6]([NH2:21])[N:5]=[C:4]([N:22]2[C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[C:24]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[F:38])=[N:23]2)[N:3]=1.[H-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[NH2:1][C:2]1[N:3]=[C:4]([N:22]2[C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[C:24]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[F:38])=[N:23]2)[N:5]=[C:6]2[C:7]=1[N:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:9](=[O:10])[NH:21]2

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 57330719Methyl {4,6-diamino-2-[3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidin-5-yl}(4-fluorobenzyl)carbamate

生成物 1

HCID 569289446-Amino-7-(4-fluorobenzyl)-2-[3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-7,9-dihydro-8H-purin-8-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

21 mg (0.04 mmol) of the compound from example 50A were initially charged in tetrahydrofuran (1.0 ml), 1.8 mg (0.04 mmol) of sodium hydride (60% in mineral oil) were added and the mixture was stirred at 65° C. for 30 min. The reaction mixture was admixed with saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue was separated by means of preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient) and the product fractions were concentrated. This gave 8.5 mg (44% of theory) of the title compound in solid form.

後処理

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was separated by means of preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient)
  6. concentrationthe product fractions were concentrated

出典と根拠

ORDレコード
ord-62178f1627f846bb9d04ba53f261a0b0
出典データセット
uspto-grants-2015_08
特許番号
US09096592B2

反応ノート

読み込み中…