Triphenylphosphine → 9-benzyloxy-2-isopropyl-6-(1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169296
O[CH2:2][CH2:3][N:4]([CH:35]([CH3:37])[CH3:36])[C:5]([C:7]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([OH:21])[N:10]=[C:9]([CH2:22][C:23]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:14]([O:13][C:12]1[C:11](=[O:21])[N:10]=[C:9]([CH2:22][C:23]2([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[N:8]2[CH2:2][CH2:3][N:4]([CH:35]([CH3:37])[CH3:36])[C:5](=[O:6])[C:7]=12)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 178457437HCID 178457437, Verbindung

Produkt 1

HCID 867259429-benzyloxy-2-isopropyl-6-(1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (258) (0.43 g, 0.85 mmol) and triphenyl phosphine (0.45 g, 1.71 mmol) in dry dichloromethane (10.0 mL) was added diethyl azidocarboxylate (0.34 mL, 2.13 mmol) at room temperature and the reaction stirred for 2 h. After completion of the reaction, the solvent was evaporated and the crude product was purified by normal silica gel column chromatography (using 2% methanol in dichloromethane) to get 9-benzyloxy-2-isopropyl-6-(1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (259) (0.18 g, 43.0%) as a white solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe crude product was purified by normal silica gel column chromatography (using 2% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-2dd4cb1e77414285b1b4c1348ae93ad8
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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