(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 2364717ノート

反応式

HRID 2364717 の反応式
[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

参加物

5

反応物 2

HCID 59815009(R)-methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(isopropyl)amino)butanoateHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 176Acetic Acid溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2eed172f56464660914b9bf4d77a4b28
出典データセット
uspto-grants-2014_04
特許番号
US08691822B2

反応ノート

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