Reaction equation
[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]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- temperatureWhen the reaction material has cooled
- washthe solution is washed with dilute hydrochloric acid and water
- concentrationconcentrated by evaporation
- custompurified by chromatography on silica gel (eluant: ethyl acetate/n-hexane 1:1)
Sources & evidence
- ORD record
- ord-6620fd0c65564e9481d246908b12577a
- Source dataset
- uspto-grants-1994_07
- Patent number
- US05332717
Linked notes
Loading…