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

HRID 1729158

反応式

HRID 1729158 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6569Methyl Ethyl Ketone溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6620fd0c65564e9481d246908b12577a
出典データセット
uspto-grants-1994_07
特許番号
US05332717

関連ノート

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