Ammonium Chloride → 2-Chloro-9-cyclopentyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 1044075노트

반응식

HRID 1044075 반응식
[CH:1]1([N:6]([C:13]2[C:18]([N+:19]([O-])=O)=[CH:17][N:16]=[C:15]([Cl:22])[N:14]=2)[CH2:7][CH2:8][C:9](OC)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH4+].[Cl-]>[Fe].CCO.O>[Cl:22][C:15]1[N:16]=[CH:17][C:18]2[NH:19][C:9](=[O:10])[CH2:8][CH2:7][N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:13]=2[N:14]=1

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 57940528Methyl 3-[cyclopentyl(2-chloro-5-nitropyrimidin-4-yl)amino]propanoate

생성물 1

HCID 579403592-Chloro-9-cyclopentyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one수율 43.7%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 19096565Water ethanol용매

실험 절차

Methyl 3-[cyclopentyl(2-chloro-5-nitropyrimidin-4-yl)amino]propanoate (1.00 g, 0.003 mol) and NH4Cl (1.38 g, 0.025 mol, 8.5 eq) were added to EtOH/H2O (4:1 ml, 10 ml) and the mixture heated to reflux before the portion-wise addition of iron powder (1.36 g, 0.024 mol, 8 eq). The RM was then refluxed for an additional 2 h. Progress of the reaction was monitored by HPLC and when no SM remained the RM was filtered hot through celite. The celite was washed with EtOAc (10 ml) and EtOH (10 ml) [both hot] and the filtrate evaporated under reduced pressure and further dried in vacuo to give the product as a brown solid (350 mg, 43%); Rt=12 min (Vydac 1); MS+ve: 267.2.

후처리

  1. temperaturethe mixture heated
  2. temperatureThe RM was then refluxed for an additional 2 h
  3. filtrationwas filtered hot through celite
  4. washThe celite was washed with EtOAc (10 ml) and EtOH (10 ml) [both hot] and the filtrate
  5. customevaporated under reduced pressure
  6. customfurther dried in vacuo

출처 및 근거

ORD 기록
ord-c40e0962d7ba4be1ae6557104c617643
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563542B2

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