9-Hydroxy-7-isopropyl-2-(2-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione → 9-hydroxy-7-isopropyl-2-(1-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

HRID 1162811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162811
[OH:1][C:2]1[C:7](=[O:8])[N:6]([CH:9]([CH3:11])[CH3:10])[C:5](=[O:12])[N:4]2[CH2:13][CH2:14][N:15]([CH2:18][CH:19]=[CH2:20])[C:16](=[O:17])[C:3]=12>CCO.O.[Rh](Cl)(Cl)Cl>[OH:1][C:2]1[C:7](=[O:8])[N:6]([CH:9]([CH3:10])[CH3:11])[C:5](=[O:12])[N:4]2[CH2:13][CH2:14][N:15]([CH:18]=[CH:19][CH3:20])[C:16](=[O:17])[C:3]=12

Komponenten

4

Edukt 1

HCID 684317659-Hydroxy-7-isopropyl-2-(2-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

Produkt 1

HCID 684315469-hydroxy-7-isopropyl-2-(1-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 16211510Rhodium trichloride hydrateKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 9-hydroxy-7-isopropyl-2-(2-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione (3.0 g, 11 mmol) and rhodium trichloride hydrate (200 mg, 1 mmol) in EtOH (75 mL) was heated to reflux for 8 h. The reaction was cooled to ambient temperature and the solvent was removed in vacuo. The reddish solid was triturated in MeOH and collected by filtration to give the title compound as a solid. HPLC RT=2.90 min (Method A); ES MS (M+H)=280; 1H NMR (400 MHz, DMSO-d6) δ 11.59 (s, 1H), 7.10 (d, J=4.5 Hz, 1H), 5.49 (sextet, J=6 Hz, 1H), 5.04 (septet, J=7 Hz, 1H), 3.97 (m, 2H), 3.79 (m, 2H), 1.76 (d, J=6 Hz, 3H), 1.39 (d, J=7 Hz, 6H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 8 h
  3. customthe solvent was removed in vacuo
  4. customThe reddish solid was triturated in MeOH
  5. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-805c836bfd844861a5e86645e41bea7d
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820680B2

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