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

HRID 600403노트

반응식

HRID 600403 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-61ef08dffc004c12a2c5a59d2d73804e
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902187B2

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