Hydrochloric Acid → 3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-1,5,6,7-tetrahydro-2H-cyclopenta[d]pyrimidine-2,4(3H)-dione

HRID 1722937Notes

Reaction equation

HRID 1722937 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([NH:12][C:13](=[O:25])[NH:14][C:15]2[CH2:19][CH2:18][CH2:17][C:16]=2[C:20](OCC)=[O:21])=[C:4]([F:26])[CH:3]=1.C[O-].[Na+].Cl>CO>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]2[C:20](=[O:21])[C:16]3[CH2:17][CH2:18][CH2:19][C:15]=3[NH:14][C:13]2=[O:25])=[C:4]([F:26])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 20026019HCID 20026019, compound

Product 1

HCID 200260343-(4-chloro-2-fluoro-5-isopropoxyphenyl)-1,5,6,7-tetrahydro-2H-cyclopenta[d]pyrimidine-2,4(3H)-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 6.0 g of ethyl 2-[3-(4-chloro-2-fluoro-5-isopropoxyphenyl)ureido]-1-cyclopentenecarboxylate in 100 ml of absolute methanol is treated while stirring at room temperature with 7.8 ml of 2N sodium methylate solution and the reaction mixture is stirred for 2 hours. The solution is treated with 7.8 ml of 2N hydrochloric acid and evaporated to dryness. The residue is dissolved in 200 ml of ethyl acetate and the solution is washed with water, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is recrystallized from methylene chloride/diethyl ether. There is obtained 3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-1,5,6,7-tetrahydro-2H-cyclopenta[d]pyrimidine-2,4(3H)-dione, m.p. 215°-217° C.

Workup

  1. additionis treated
  2. customevaporated to dryness
  3. dissolutionThe residue is dissolved in 200 ml of ethyl acetate
  4. washthe solution is washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue is recrystallized from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-b577cd24214e4fb2af649640b720ec14
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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