Methanol → 9-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-cyclopropylmethyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169367Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169367
[CH:1]1([CH2:4][N:5]([CH2:36][CH2:37]O)[C:6]([C:8]2[C:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]3([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[CH2:28][CH2:27][CH2:26][CH2:25]3)[N:9]=2)=[O:7])[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.CO>ClCCl.C(OCC)(=O)C>[CH2:15]([O:14][C:13]1[C:12](=[O:22])[N:11]=[C:10]([CH2:23][C:24]2([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[CH2:25][CH2:26][CH2:27][CH2:28]2)[N:9]2[CH2:37][CH2:36][N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[C:6](=[O:7])[C:8]=12)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178519972HCID 178519972, Verbindung

Produkt 1

HCID 867259989-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-cyclopropylmethyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid cyclopropylmethyl-(2-hydroxyethyl)-amide (330) (390 mg, 0.73 mmol) in dichloromethane (30 mL) was added triphenyl phosphine (286 mg, 1.09 mmol) and diisopropyl azodicarboxylate (0.22 mL, 1.09 mmol) at room temperature the reaction was stirred for 30 minutes (TLC; 5% methanol in ethyl acetate/UV/SiO2, Rf=0.05). The dichloromethane was removed in vacuo and the crude mass was purified by silica gel (normal, 100-200 mesh) column chromatography using gradient eluent of 1% to 5% methanol in dichloromethane to get pure 9-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-cyclopropylmethyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (331) (280 mg, 74%) as a white sticky solid.

Aufarbeitung

  1. customThe dichloromethane was removed in vacuo
  2. customthe crude mass was purified by silica gel (normal, 100-200 mesh) column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b2944dff281642f7ba150799bf8ecc06
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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