(Rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclobutyl-amino]-2-methyl-propanoic acid methyl ester → HCID 87555122, Verbindung

HRID 2111378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111378
C[O:2][C:3](=O)[CH:4]([CH3:21])[CH2:5][N:6]([C:11]1[C:16]([N+:17]([O-])=O)=[CH:15][N:14]=[C:13]([Cl:20])[N:12]=1)[CH:7]1[CH2:10][CH2:9][CH2:8]1>[Fe].C(O)(=O)C>[Cl:20][C:13]1[N:14]=[CH:15][C:16]2[NH:17][C:3](=[O:2])[CH:4]([CH3:21])[CH2:5][N:6]([CH:7]3[CH2:10][CH2:9][CH2:8]3)[C:11]=2[N:12]=1

Komponenten

4

Edukt 1

HCID 87619097(Rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclobutyl-amino]-2-methyl-propanoic acid methyl ester

Produkt 1

HCID 87555122HCID 87555122, VerbindungAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 2.54 g (0.0077 mole) of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclobutyl-amino]-2-methyl-propanoic acid methyl ester (IV-52) and 40 mL of acetic acid was added 2.5 g (0.0448 g-atom) of iron powder. The mixture was heated at 80 degrees for 3 hours, then filtered through Celite while still hot. The filter cake was washed with 100 mL of ethyl acetate. The filtrate was washed successively with 100 mL of water, 100 mL of 7.4 M ammonium hydroxide, 100 mL of water and 100 mL of brine. The aqueous layers were back extracted with 100 mL of ethyl acetate. The ethyl acetate layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from dichloromethane—hexanes to give 1.07 g of (rac)-2-chloro-9-cyclobutyl-7-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-52) as white crystalline solid.

Aufarbeitung

  1. temperatureThe mixture was heated at 80 degrees for 3 hours
  2. filtrationfiltered through Celite while still hot
  3. washThe filter cake was washed with 100 mL of ethyl acetate
  4. washThe filtrate was washed successively with 100 mL of water, 100 mL of 7.4 M ammonium hydroxide, 100 mL of water and 100 mL of brine
  5. extractionThe aqueous layers were back extracted with 100 mL of ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from dichloromethane—hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b5fa6c3fb73743038b956bc805d197dd
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517873B2

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