(R)-methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(isopropyl)amino)butanoate → (R)-2-chloro-7-ethyl-8-isopropyl-7,8-dihydropteridin-6(5H)-one

HRID 2364717노트

반응식

HRID 2364717 반응식
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH:16]([CH3:18])[CH3:17])[C@H:9]([CH2:14][CH3:15])[C:10](OC)=[O:11])[C:5]([N+:19]([O-])=O)=[CH:4][N:3]=1.[H][H]>C(O)(=O)C.[Ni]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:19][C:10](=[O:11])[C@@H:9]([CH2:14][CH3:15])[N:8]([CH:16]([CH3:18])[CH3:17])[C:6]=2[N:7]=1

참가 물질

5

반응물 2

HCID 59815009(R)-methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(isopropyl)amino)butanoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 11572412(R)-2-chloro-7-ethyl-8-isopropyl-7,8-dihydropteridin-6(5H)-one수율 206.5%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 176Acetic Acid용매

반응 조건

온도
75 °C

실험 절차

Methyl (2R)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate 22b (7.30 g, 23 mmol) was dissolved in 100 mL acetic acid followed by the addition of 5 g Raney nickel, repeated filled with hydrogen for three times. The reaction mixture was heated to 75° C., stirred for 2 hours and filtered. The filtrate was concentrated under reduced pressure, added with 30 mL of ice water resulting in the formation of precipitate. The precipitate was filtered. the filter cake was dried by heat to obtain the crude title compound (7R)-2-chloro-7-ethyl-8-isopropyl-5,7-dihydropteridin-6-one 22c (12.10 g, yield: 71.7%) as a gray solid, which was used in the next step without further furification.

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionadded with 30 mL of ice water resulting in the formation of precipitate
  4. filtrationThe precipitate was filtered
  5. customthe filter cake was dried
  6. temperatureby heat

출처 및 근거

ORD 기록
ord-2eed172f56464660914b9bf4d77a4b28
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691822B2

반응 노트

불러오는 중…