Acetic Acid → ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d] pyrimidin-3-yl)-benzoate

HRID 845924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 845924
[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([N:13]2[C:18](=[O:19])[C:17]3[CH2:20][CH2:21][CH2:22][C:16]=3[NH:15][C:14]2=[O:23])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].CI.[C:28](O)(=O)C>COCCOC>[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([N:13]2[C:18](=[O:19])[C:17]3[CH2:20][CH2:21][CH2:22][C:16]=3[N:15]([CH3:28])[C:14]2=[O:23])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21270732ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate

Produkt 1

HCID 20130616ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d] pyrimidin-3-yl)-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

A solution of 50.2 g of ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate in 300 ml of absolute 1,2-dimethoxyethane is added dropwise while stirring at 20° C. during 10 minutes to a suspension of 3.6 g of sodium hydride in 100 ml of absolute 1,2-dimethoxyethane. The reaction mixture is stirred for 1 hour, treated with 21.3 g of methyl iodide and stirred for a further 2 hours. The mixture is subsequently rendered neutral with 0.5 ml of acetic acid and evaporated to dryness under reduced pressure. The residue is dissolved in 500 ml of ethyl acetate, the solution shaken three times with 250 ml of water, and the organic phase is dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is dissolved in 50 ml of hot methylene chloride, seeded, and treated with diethyl ether. There is obtained ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d] pyrimidin-3-yl)-benzoate, m.p. 141°-143° C.

Aufarbeitung

  1. stirringstirred for a further 2 hours
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue is dissolved in 500 ml of ethyl acetate
  4. stirringthe solution shaken three times with 250 ml of water
  5. dry with materialthe organic phase is dried over anhydrous sodium sulphate
  6. customevaporated to dryness under reduced pressure
  7. dissolutionThe residue is dissolved in 50 ml of hot methylene chloride
  8. additiontreated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-510d50ef252d4bad9fdbd8e4473fe0e4
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04760163

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