tert-Butyl (3-aminopropyl)carbamate → tert-butyl N-[3-[1-(5-benzyl-3-methyl-4-oxo-[1,2]oxazolo[5,4-d]pyrimidin-6-yl)propylamino]propyl]carbamate

HRID 1794594

Reaktionsgleichung

Reaktionsgleichung von HRID 1794594
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][O:17][C:11]=2[N:10]=[C:9]1[CH:19](Br)[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([NH:30][CH2:31][CH2:32][CH2:33][NH2:34])([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>CCO>[C:26]([O:25][C:23](=[O:24])[NH:30][CH2:31][CH2:32][CH2:33][NH:34][CH:19]([C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][O:17][C:11]=2[N:10]=1)[CH2:20][CH3:21])([CH3:29])([CH3:27])[CH3:28]

Komponenten

4

Edukt 2

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 222223445-Benzyl-6-(1-bromo-propyl)-3-methyl-5h-isoxazolo[5,4-d]pyrimidin-4-one

Produkt 1

HCID 57587937tert-butyl N-[3-[1-(5-benzyl-3-methyl-4-oxo-[1,2]oxazolo[5,4-d]pyrimidin-6-yl)propylamino]propyl]carbamateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution the compound of Example 1 Step 4 (200 mg, 0.55 mmol) in EtOH (25 mL) was treated with N-BOC-1,3-diaminopropane (240 mg, 1.38 mmol) and stirred at reflux for 6 h. The mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by flash chromatography on SiO2 (50% EtOAc/Hexane) to afford the desired product as a yellow oil (165 mg, 66%); 1H NMR (DMSO-d6) δ 7.35 (m, 5H), 5.47 (m, 2H), 4.67 (s, 1H), 2.84 (m, 2H), 2.54 (m, 2H), 2.50 (s, 3H), 1.83 (m, 2H), 1.60 (m, 2H), 1.37 (s, 9H), 0.71 (m, 3H); (LC/MS (ESI): 456 (M+H)+.

Aufarbeitung

  1. temperatureat reflux for 6 h
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash chromatography on SiO2 (50% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3436424e7479451aa797a277c2ba6a73
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022850B2

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