methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]butanoate → (7S)-2-chloro-8-cyclopentyl-7-ethyl-5,7-dihydropteridin-6-one

HRID 2364756노트

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HRID 2364756 반응식
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C@@H:9]([CH2:14][CH3:15])[C:10](OC)=[O:11])[C:5]([N+:21]([O-])=O)=[CH:4][N:3]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:21][C:10](=[O:11])[C@H:9]([CH2:14][CH3:15])[N:8]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:6]=2[N:7]=1

참가 물질

4

반응물 1

HCID 86668255methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]butanoate

생성물 1

HCID 86668256(7S)-2-chloro-8-cyclopentyl-7-ethyl-5,7-dihydropteridin-6-one수율 92%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
65 °C

실험 절차

Methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]butanoate 41d (14.17 g, 41.33 mmol) was dissolved in 300 mL of acetic acid followed by the addition of iron powder (9 g, 0.17 mol). After exothermic reaction was completed, the reaction solution was heated to 65° C., and stirred for 1.5 hours. The reaction mixture was filtered and the filter cake was washed with dichloromethane (350 mL). The filtrate was concentrated under reduced pressure, added with 150 mL of water and filtered. The filter cake was washed with water (60 mL×3) and the mixture solvent of hexane and acetone (V/V=6:1) (140 mL) successively. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain the title compound (7S)-2-chloro-8-cyclopentyl-7-ethyl-5,7-dihydropteridin-6-one 41e (10.67 g, yield: 92.0%) as a light yellow solid.

후처리

  1. customAfter exothermic reaction
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was washed with dichloromethane (350 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionadded with 150 mL of water
  6. filtrationfiltered
  7. washThe filter cake was washed with water (60 mL×3)
  8. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2b73a324c9104174a89a9f9fb2166c92
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691822B2

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