Triphenylphosphine → {1-[(1S,4R)-4-(2,6-Dichloro-purin-9-yl)cyclopent-2-enyl]-1H-pyrazol-4-yl}-methanol

HRID 1929773Notizen

Reaktionsgleichung

C(OC(=O)O[C@H:6]1[CH2:10][C@@H:9]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][C:14]([Cl:21])=[N:15][C:16]=3[Cl:20])[CH:8]=[CH:7]1)C.[NH:23]1[CH:27]=[C:26]([CH2:28][OH:29])[CH:25]=[N:24]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:21][C:14]1[N:13]=[C:12]2[C:17]([N:18]=[CH:19][N:11]2[C@@H:9]2[CH2:10][C@H:6]([N:23]3[CH:27]=[C:26]([CH2:28][OH:29])[CH:25]=[N:24]3)[CH:7]=[CH:8]2)=[C:16]([Cl:20])[N:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture comprising carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester (Intermediate AA2) (1.00 g, 2.92 mmol), (1H-pyrazol-4-yl)-methanol (preparation shown below) (0.34 g, 3.50 mmol) and triphenyl phosphine (0.115 g, 0.44 mmol) in deoxygenated THF (10 mL) under an inert atmosphere of argon is treated with tris(dibenzylideneacetone)dipalladium(0) (0.13 g, 0.15 mmol) and stirred at 50° C. for 1 hour. The solvent is removed in vacuo and the crude product is purified by chromatography on silica eluting with MeOH/DCM (1:25) to yield the title compound.

Aufarbeitung

customThe solvent is removed in vacuo
customthe crude product is purified by chromatography on silica eluting with MeOH/DCM (1:25)

Quellen und Nachweise

ORD-Eintrag: ord-7a6062a1c7ae49f09497b2dbedb957b1
Quelldatensatz: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08188100B2

Notizen zur Reaktion

Wird geladen…