Sodium Iodide → 3-Cyanomethoxy-7-[(4,6-dimethoxypyrimidin-2-yl)oxy]-phthalide

HRID 1729158

반응식

HRID 1729158 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[C:19](=[O:20])[O:18][CH:17]3[OH:22])[N:4]=1.Cl[CH2:24][C:25]#[N:26].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].C1OCCOCCOCCOCCOCCOC1>CC(CC)=O.COC(C)(C)C>[C:25]([CH2:24][O:22][CH:17]1[C:16]2[C:21](=[C:12]([O:11][C:5]3[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]=3)[CH:13]=[CH:14][CH:15]=2)[C:19](=[O:20])[O:18]1)#[N:26]

참가 물질

8

반응물 5

HCID 5238Sodium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 199274177-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxy-phthalide

생성물 1

HCID 199274253-Cyanomethoxy-7-[(4,6-dimethoxypyrimidin-2-yl)oxy]-phthalide

시약·촉매·용매 2

HCID 6569Methyl Ethyl Ketone용매HCID 15413tert-Butyl methyl ether용매

실험 절차

A mixture of 1.5 g of 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxy-phthalide (see Example 84) and 0.8 ml of chloroacetonitrile is maintained at 60° C. for 1 hour in ethyl methyl ketone in the presence of 2.1 g of dry potassium carbonate and a spatula tip each of sodium iodide and 18-crown-6. When the reaction material has cooled, it is taken up in tert-butyl methyl ether and the solution is washed with dilute hydrochloric acid and water, concentrated by evaporation and purified by chromatography on silica gel (eluant: ethyl acetate/n-hexane 1:1) to yield 3-cyanomethoxy-7-[(4,6-dimethoxypyrimidin-2-yl)oxy]-phthalide, m.p. 99°-102° C.

후처리

  1. temperatureWhen the reaction material has cooled
  2. washthe solution is washed with dilute hydrochloric acid and water
  3. concentrationconcentrated by evaporation
  4. custompurified by chromatography on silica gel (eluant: ethyl acetate/n-hexane 1:1)

출처 및 근거

ORD 기록
ord-6620fd0c65564e9481d246908b12577a
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05332717

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