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

HRID 22166
Notes
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Reaction equation

HRID 22166 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 15413tert-Butyl methyl etherSolvent

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-dimethoxy-pyrimidin-2-yl)oxy]-phthalide, m.p. 99°-102° C.

Workup

  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)

Sources & evidence

ORD record
ord-e37d68f706bd42cbb3420ee6f343d04d
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05428002

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes