Hydrochloric Acid → HCID 178518396, compound

To a suspension of ethyl 2-oxocyclopentanecarboxylate (10 mL, 67.2 mmol) and urea (6.07 g, 101 mmol) in EtOH (20 mL), cooled in an ice-bath, was added concentrated HCl (1 mL) dropwise. After completion of addition, the ice bath was removed and the reaction mixture was stirred at RT for 30 min. The reaction mixture was then heated to reflux at 85° C. for 5 h. The reaction mixture was cooled to RT and the EtOH was decanted to give a crystalline solid. The solid was heated to reflux with aqueous 5% NaOH solution (25 mL) for 2 h. The reaction mixture was cooled to RT and the precipitate was collected by filtration. The precipitate was washed with water and dried to afford 6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol (5.36 g, 52% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 1.81-1.97 (m, 2H), 2.38-2.46 (m, 2H), 2.47-2.60 (m, 2H), 10.70 (s, 1H), 11.05 (s, 1H).

1. temperaturecooled in an ice-bath
2. additionAfter completion of addition
3. customthe ice bath was removed
4. temperatureThe reaction mixture was then heated
5. temperatureto reflux at 85° C. for 5 h
6. temperatureThe reaction mixture was cooled to RT
7. customthe EtOH was decanted
8. customto give a crystalline solid
9. temperatureThe solid was heated
10. temperatureThe reaction mixture was cooled to RT
11. filtrationthe precipitate was collected by filtration
12. washThe precipitate was washed with water
13. customdried

ORD record

ord-b4ee0a844f8e4ccb8a7062d5282f46c2

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422267B2