1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 9-Cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

HRID 79106

Reaktionsgleichung

Cl[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([NH:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>O1CCOCC1.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]>[CH:16]1([N:15]2[C:9]3[N:10]=[C:11]([NH2:14])[N:12]=[CH:13][C:8]=3[C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]2=3)[CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To a solution of 3 (2.3 g, 7.9 mmol) in dioxane (60 mL) were added tris(dibenzylideneacetone)dipalladium (0) (368 mg, 0.4 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (696 mg, 1.2 mmol), and sodium t-butoxide (1.15 g, 12 mmol). The mixture thus obtained was heated at 150° C. under microwave irradiation for 3 h. The reaction mixture was passed through a short pack silica gel column and concentrated. The residue was purified by flash chromatography on silica gel eluting with 2% methanol in dichloromethane to give the title compound (4) as a white solid (1.71 g, 85%). 1H NMR (500 MHz, DMSO-d6) δ 9.05 (1H, s), 8.87 (1H, br. s), 8.37 (1H, d, J=4.9 Hz), 7.93 (1H, d, J=5.1 Hz), 6.97 (2H, br. s), 5.33 (1H, p, J=8.6 Hz), 2.27 (2H, m), 2.04 (4H, m), 1.76 (2H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 254.1, Calculated 254.1.

Aufarbeitung

customThe mixture thus obtained
concentrationconcentrated
customThe residue was purified by flash chromatography on silica gel eluting with 2% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag: ord-105c7c0d2dd94906b59e2196449b303d
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08841312B2

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