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

HRID 643514노트

반응식

HRID 643514 반응식
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

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

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온도
75 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-968ff35886174609857221e8941abedf
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700607B2

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