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

HRID 1044075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044075
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 579403592-Chloro-9-cyclopentyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-oneAusbeute 43,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c40e0962d7ba4be1ae6557104c617643
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563542B2

Notizen zur Reaktion

Wird geladen…