Diisobutylaluminum hydride → (2-(Methylsulfanyl)pyrimidin-5-yl)methanol

HRID 1867169ノート

反応式

HRID 1867169 の反応式
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([C:9](OC)=[O:10])=[CH:5][N:4]=1.CC(C[AlH]CC(C)C)C>ClCCl>[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][N:4]=1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 11194721Methyl 2-(Methylthio)pyrimidine-5-carboxylate

生成物 1

HCID 22050485(2-(Methylsulfanyl)pyrimidin-5-yl)methanol収率 53.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-70 °C

実験手順

To a cold suspension of methyl 2-(methylthio)pyrimidine-5-carboxylate (1.74 g, 9.4 mmol) in dichloromethane (20 mL, −70° C.) was added DIBAL (20.8 mL, 20 mmol) dropwise via an addition funnel. The mixture was stirred under nitrogen at −70° C. for 1 hour and then at −50° C. for 3 hours. The reaction was diluted with dichloromethane (50 mL) and quenched with a suspension of sodium sulfate decahydrate (10 g) in water (50 mL). The slurry was filtered through celite and the filtrate was concentrated. The residue was purified by flash chromatography (silica gel) using 100% ethyl acetate to afford the desired compound (0.7813 g, 39%) as a yellow solid. 1H-NMR ((CD3OD, 400 MHz) δ 8.53 (s, 2H), 4.56 (s, 2H), 2.54 (s, 3H); ES-HRMS m/z 157.0409 (M+H C6H8N2OS requires 157.0430).

後処理

  1. waitat −50° C. for 3 hours
  2. customquenched with a suspension of sodium sulfate decahydrate (10 g) in water (50 mL)
  3. filtrationThe slurry was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash chromatography (silica gel)

出典と根拠

ORDレコード
ord-ea6ce4cc348a444f94d69b94b2f0059c
出典データセット
uspto-grants-2009_12
特許番号
US07629363B2

反応ノート

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