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

HRID 2402528Notes

Reaction equation

HRID 2402528 reaction equation
O=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9]CC)=O.[NH2:12][C:13]([NH2:15])=[O:14].Cl>CCO>[NH:12]1[C:2]2[CH2:6][CH2:5][CH2:4][C:3]=2[C:7](=[O:9])[NH:15][C:13]1=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1176UreaHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 2307426,7-Dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dioneYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-oxocyclopentanecarboxylate (15.6 g, 0.10 mol), urea (9.0 g 0.15 mol) and hydrochloric acid (37%, aqueous, 5 mL) in EtOH (100 mL) was heated to 80° C. for 24 h. The mixture was cooled to rt and the precipitate was collected by filtration and dried to afford 6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione (11.1 g, 73%) as a white solid.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-251f93e4ac83403cb73b37e3be238848
Source dataset
uspto-grants-2014_08
Patent number
US08796294B2

Reaction notes

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