Iodoethane → Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidin-5-yl}ethylcarbamate

HRID 626619ノート

反応式

HRID 626619 の反応式
[NH2:1][C:2]1[C:7](NC(=O)OC)=[C:6]([NH2:13])[N:5]=[C:4]([N:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[C:16]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:15]2)[N:3]=1.C[Si]([N-:36][Si](C)(C)C)(C)C.[Na+].I[CH2:43][CH3:44].[C:45]([O:48][CH2:49]C)(=[O:47])C>C1COCC1>[NH2:13][C:6]1[C:7]([CH2:44][CH2:43][NH:36][C:45](=[O:47])[O:48][CH3:49])=[C:2]([NH2:1])[N:3]=[C:4]([N:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[C:16]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:15]2)[N:5]=1

参加物

6

反応物 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 56963347Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo [4,3-b]pyridin-1-yl]pyrimidin-5-yl}carbamate

生成物 1

HCID 86698876Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidin-5-yl}ethylcarbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Under argon, 142 mg (0.33 mmol) of the compound from example 1 were initially charged in THF (9.5 ml), the mixture was cooled to 0° C. and 0.33 ml (0.33 mmol) of sodium bis(trimethylsilyl)amide (1.0 M in THF) was then added dropwise. The mixture was stirred at 0° C. for 30 min, and 35 μl (0.43 mmol) of iodoethane were then added dropwise. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with ethyl acetate and washed twice with saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was chromatographed on silica gel (mobile phase dichloromethane:methanol 60:1) and the product fractions were concentrated. This gave 89 mg (59% of theory) of the title compound as a solid.

後処理

  1. stirringThe reaction mixture was stirred at RT overnight
  2. washwashed twice with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (mobile phase dichloromethane:methanol 60:1)
  7. concentrationthe product fractions were concentrated

出典と根拠

ORDレコード
ord-ee831e6ded404dda843f810e2978b050
出典データセット
uspto-grants-2016_04
特許番号
US09309239B2

反応ノート

読み込み中…