Potassium Phosphate, Tribasic → 6-(2-(4-Methoxybenzyloxy)-4-methylpyridin-3-yl)quinazolin-2-amine

HRID 558461Notizen

Reaktionsgleichung

P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C(C)(C)OB([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[C:22]([NH2:27])[N:21]=[CH:20]3)O1.[CH3:29][O:30][C:31]1[CH:46]=[CH:45][C:34]([CH2:35][O:36][C:37]2[C:42](Br)=[C:41]([CH3:44])[CH:40]=[CH:39][N:38]=2)=[CH:33][CH:32]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C(O)(C)C.O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([CH2:35][O:36][C:37]2[C:42]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23]=[C:22]([NH2:27])[N:21]=[CH:20]4)=[C:41]([CH3:44])[CH:40]=[CH:39][N:38]=2)=[CH:45][CH:46]=1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

To a mixture of potassium phosphate (2.07 g, 9.73 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine (1.06 g, 3.89 mmol), 2-(4-methoxybenzyloxy)-3-bromo-4-methylpyridine (1.000 g, 3.24 mmol), and S—PHOS (0.162 mmol) in isopropyl alcohol (21 mL) and water (7 mL) was added palladium acetate (0.0364 g, 0.162 mmol). The mixture was stirred at 75° C. After 4 hrs, the reaction mixture was diluted with EtOAc (ca. 100 mL) and washed with water and brine. After drying with sodium sulfate, the organic fraction was stripped onto silica and purified by silica gel chromatography using 1-8% MeOH in CH2Cl2 w/NH4OH to provide 6-(2-(4-methoxybenzyloxy)-4-methylpyridin-3-yl)quinazolin-2-amine as a tan solid. M+H+=373.1.

Aufarbeitung

washwashed with water and brine
dry with materialAfter drying with sodium sulfate
custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-5034f40c2b7743fc9fc9fb201ba377e3
Quelldatensatz: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08063055B2

Notizen zur Reaktion

Wird geladen…