Trifluoroacetic acid → (+/-)-2-[1-(2-amino-2-methyl-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-pteridin-4-one

HRID 1823673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1823673
C(OC(=O)[NH:7][C:8]([CH3:35])([CH3:34])[CH2:9][NH:10][CH:11]([C:15]1[N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](=[O:32])[C:22]2[C:17](=[N:18][C:19]([Cl:33])=[CH:20][N:21]=2)[N:16]=1)[CH:12]([CH3:14])[CH3:13])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]([CH3:35])([CH3:34])[CH2:9][NH:10][CH:11]([C:15]1[N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](=[O:32])[C:22]2[C:17](=[N:18][C:19]([Cl:33])=[CH:20][N:21]=2)[N:16]=1)[CH:12]([CH3:14])[CH3:13]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86592840(+/-)-{2-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propylamino]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 22172622(+/-)-2-[1-(2-amino-2-methyl-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-pteridin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Formula 202 where R2 is H; R3 is Cl; R5 is Benzyl; R6 is Isopropyl; R6′ is H; Ra and Rb are Methyl; W and Z are —N═; X and Y are —C═: To a solution of (±)-{2-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propylamino]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (1.63 g, 3.16 mmol) in dichloromethane (40 mL) is added trifluoroacetic acid (10 mL). The resultant solution is maintained at ambient temperature overnight and concentrated under reduced pressure. The residue is dissolved in dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate (40 mL). The aqueous layer is extracted with dichloromethane (50 mL) and the combined extracts are dried over magnesium sulfate, filtered and concentrated under reduced pressure to give (±)-2-[1-(2-amino-2-methyl-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-pteridin-4-one which is used in the subsequent step without purification.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue is dissolved in dichloromethane (50 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (40 mL)
  4. extractionThe aqueous layer is extracted with dichloromethane (50 mL)
  5. dry with materialthe combined extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-165b6ffbf6964635820165e0d89c1ea7
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07038048B2

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