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

HRID 558461Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-5034f40c2b7743fc9fc9fb201ba377e3
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063055B2

Reaction notes

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