Sodium hydride → 6-[2-(5-Bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine

HRID 2306

반응식

HRID 2306 반응식
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[H-].[Na+].[Br:21][C:22]1[CH:23]=[N:24][C:25](Cl)=[N:26][CH:27]=1.[Cl-].[NH4+]>O1CCCC1>[Br:21][C:22]1[CH:23]=[N:24][C:25]([O:11][CH2:10][CH2:9][O:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=2[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[N:26][CH:27]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 6066655-Bromo-2-chloropyrimidineHCID 111182972-{6-Amino-5-(4-methylphenyl)-pyrimidin-4-yloxy}ethanol

생성물 1

HCID 117291026-[2-(5-Bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine수율 91.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-{6-amino-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (7.54 g) in tetrahydrofuran (150 ml) is added sodium hydride (60% dispersion-type, 1.47 g), and thereto is added 5-bromo-2-chloropyrimidine (7.73 g), and the mixture is stirred at room temperature overnight. To the reaction solution is added saturated aqueous ammonium chloride solution, and the mixture is evaporated to remove the solvent. The precipitated crystals are collected by filtration, washed and dried. The crude crystals are purified by silica gel column chromatography (solvent; chloroform/methanol=100:1~80:1), and recrystallized from tetrahydrofuran/diethyl ether to give 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (11.27 g).

후처리

  1. customthe mixture is evaporated
  2. customto remove the solvent
  3. filtrationThe precipitated crystals are collected by filtration
  4. washwashed
  5. customdried
  6. customThe crude crystals are purified by silica gel column chromatography (solvent; chloroform/methanol=100:1~80:1)
  7. customrecrystallized from tetrahydrofuran/diethyl ether

출처 및 근거

ORD 기록
ord-a7b7ef5f674140eda2b87b65e3637f7d
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728706

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