Solketal → HCID 14776421、化合物

HRID 520490

反応式

HRID 520490 の反応式
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].Cl[C:13]1[N:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=1>C1COCC1>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][O:8][C:13]2[N:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=2)[CH2:4][O:3]1

参加物

5

反応物 3

HCID 7528SolketalHCID 24758Sodium hydrideHCID 3457522-Chloro-4-aminopyrimidine

生成物 1

HCID 14776421HCID 14776421、化合物収率 70.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of solketal 58 (34.4 g, 260 mmol) in THF (150 mL) was added NaH (10.4 g, 260 mmol) at room temperature and the mixture stirred for 1 h. 2-chloro-4-aminopyrimidine 97 (15.0 g, 115 mmol) was then added, and the mixture was stirred at 70° C. for 48 h. The reaction mixture was concentrated and the crude residue was purified by flash chromatography (dichloromethane:methanol=15:1-10:1) to give 98 (18.2 g, 70% yield) as an oil. The acetonide protecting group could be removed after coupling with the appropriate aniline by treatment with EtOH/3 N HCl (4:1) at reflux for 12 h.

後処理

  1. stirringthe mixture was stirred at 70° C. for 48 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude residue was purified by flash chromatography (dichloromethane:methanol=15:1-10:1)

出典と根拠

ORDレコード
ord-aa4df939c7c242ba906436663f2ebe95
出典データセット
uspto-grants-2016_05
特許番号
US09326986B2

関連ノート

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