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

HRID 558461ノート

反応式

HRID 558461 の反応式
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

参加物

9

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 160861386-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amineHCID 670001042-(4-Methoxybenzyloxy)-3-bromo-4-methylpyridine

生成物 1

HCID 669999546-(2-(4-Methoxybenzyloxy)-4-methylpyridin-3-yl)quinazolin-2-amine

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  1. washwashed with water and brine
  2. dry with materialAfter drying with sodium sulfate
  3. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-5034f40c2b7743fc9fc9fb201ba377e3
出典データセット
uspto-grants-2011_11
特許番号
US08063055B2

反応ノート

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