Sulfur → 4-amino-3-(6-chloro-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purin-2-ylamino)benzonitrile

HRID 600403ノート

反応式

HRID 600403 の反応式
[Cl:1][C:2]1[N:10]=[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=2[N+:20]([O-])=O)[C:15]#[N:16])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:29])[N:6]2[CH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.[S]>C(OCC)(=O)C>[NH2:20][C:19]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[NH:11][C:9]1[N:8]=[C:7]2[C:3]([NH:4][C:5](=[O:29])[N:6]2[CH:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[C:2]([Cl:1])[N:10]=1

参加物

4

反応物 2

HCID 5362487SulfurHCID 866229343-(6-chloro-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purin-2-ylamino)-4-nitrobenzonitrile

生成物 1

HCID 866229354-amino-3-(6-chloro-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purin-2-ylamino)benzonitrile収率 86%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Pale yellow solid. 86% yield on 0.49 mmol scale. In a typical procedure, to 3-(6-chloro-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purin-2-ylamino)-4-nitrobenzonitrile (0.49 mmol) was added ethyl acetate (20 mL) and Pt catalyst, 0.5% sulfur (Alfa Aesar) (95.5 mg 5% on activated carbon, 4.8 mg, 0.025 mmol, 0.05 equiv.) with stirring at room temperature under hydrogen (1 atm) for 18 h (HPLC monitoring). Filtration of the reaction mixture over a small plug of celite, thorough washing with ethyl acetate and methanol, evaporation of solvent and drying provided the desired product, which was used in the next step without further purification. Yield quantitative on 2.95 mmol scale. The catalyst was washed with 12-15 portions of 100 mL of a 1/1 (v) solution of methylene chloride/isopropanol to recover desired product. MS (EI) m/z 386.1 (MH)+.

後処理

  1. filtrationFiltration of the reaction mixture over a small plug of celite
  2. washthorough washing with ethyl acetate and methanol, evaporation of solvent
  3. customdrying

出典と根拠

ORDレコード
ord-61ef08dffc004c12a2c5a59d2d73804e
出典データセット
uspto-grants-2011_03
特許番号
US07902187B2

反応ノート

読み込み中…