2-cyclopropyl-1H-imidazole → (R)-8-cyclopentyl-2-(2-cyclopropyl-1H-imidazol-1-yl)-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

HRID 44889

Reaktionsgleichung

Reaktionsgleichung von HRID 44889
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]([CH2:14][CH3:15])[N:5]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:4]=2[N:3]=1.[CH:21]1([C:24]2[NH:25][CH:26]=[CH:27][N:28]=2)[CH2:23][CH2:22]1>[Pd]>[CH:16]1([N:5]2[C:4]3[N:3]=[C:2]([N:25]4[CH:26]=[CH:27][N:28]=[C:24]4[CH:21]4[CH2:23][CH2:22]4)[N:11]=[CH:10][C:9]=3[N:8]([CH3:12])[C:7](=[O:13])[C@H:6]2[CH2:14][CH3:15])[CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

4

Edukt 2

HCID 179423832-cyclopropyl-1H-imidazoleHCID 24820413(R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

Produkt 1

HCID 58405469(R)-8-cyclopentyl-2-(2-cyclopropyl-1H-imidazol-1-yl)-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

Intermediate B was reacted via palladium coupling with 2-cyclopropyl-1H-imidazole (synthesized according to U.S. Pat. No. 6,610,723, column 91, Example 409, the disclosure of which is hereby incorporated by reference with respect to this compound) to provide the title compound. 1H NMR (CD3OD) δ: 8.05 (s, 1H), 8.04 (d, J=2.2 Hz, 1H), 7.46 (d, J=2.2 Hz, 1H), 4.43 (pent, J=3.7 Hz, 2H), 3.40 (s, 3H), 3.21 (pent, J=3.3 Hz, 1H), 2.20-2.05 (m, 1H), 2.05-1.77 (m, 7H), 1.75-1.60 (m, 2H), 1.36 (d, J=7.5 Hz, 2H), 1.30-1.10 (m, 2H), 0.87 (t, J=7.5 Hz, 3H); LCMS: 367.1 m/z (M+H)+; ret. Time: 6.70 min (Analytical Method C).

Aufarbeitung

  1. customsynthesized

Quellen und Nachweise

ORD-Eintrag
ord-12623be93dd243adbe73b39f5553d9ee
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541418B2

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