Acetone → 2-(7-benzenesulfonyl-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-propan-2-ol

HRID 334175ノート

反応式

HRID 334175 の反応式
C([N-]C(C)C)(C)C.[Li+].[C:9]1([S:15]([N:18]2[C:22]3[N:23]=[C:24]([Cl:28])[N:25]=[C:26]([Cl:27])[C:21]=3[CH:20]=[CH:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:29][C:30]([CH3:32])=[O:31]>C1COCC1>[C:9]1([S:15]([N:18]2[C:22]3[N:23]=[C:24]([Cl:28])[N:25]=[C:26]([Cl:27])[C:21]=3[CH:20]=[C:19]2[C:30]([OH:31])([CH3:32])[CH3:29])(=[O:16])=[O:17])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

5

反応物 3

HCID 180AcetoneHCID 2724682Lithium diisopropylamideHCID 252311632,4-Dichloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 866673862-(7-benzenesulfonyl-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-propan-2-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Lithium diisopropylamide (2 mL, 4.0 mmol, 2 M in THF) was added dropwise to a solution of 7-benzenesulfonyl-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (656 mg, 2.0 mmol) in anhydrous THF (15 mL) at −78° C. The resulting solution was stirred at −78° C. for 90 min, then acetone (0.4 mL, 5.5 mmol) was added and the reaction mixture was stirred at −78° C. for 30 min. The reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated in vacuo affording 2-(7-benzenesulfonyl-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-propan-2-ol. To a solution of 2-(7-benzenesulfonyl-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-propan-2-ol (2 mmol) in a mixture of isopropyl alcohol (11 mL) and water (3 mL) was added sodium hydroxide (6 mL, 36 mmol, 6M aqueous solution). The resulting mixture was stirred at RT for 2 h, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, gradient 0 to 40% ethyl acetate in cyclohexane) affording 2-(2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-propan-2-ol (304 mg, 64%). LCMS (method A): RT=2.70 min, [M]−=244/246.

後処理

  1. stirringthe reaction mixture was stirred at −78° C. for 30 min
  2. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-210201c4aa834dfd96931a4d6d034e50
出典データセット
uspto-grants-2014_11
特許番号
US08883799B2

反応ノート

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