Cyclopentanecarboximidamide → 2-cyclopentyl-6-ethylpyrimidin-4(3H)-one

Temperature

85 °C

A solution of cyclopentanecarboximidamide (8.5 g, 75.8 mmol) in ethanol (150 mL) was treated with ethyl propionaylacetate (13.7 g, 94.7 mmol), followed by the addition of sodium methoxide (4.9 g, 90.9 mmol). The mixture was then heated to 85° C. overnight. After this time, the mixture was cooled and concentrated to a volume of approximately 50 mL. Then, 2M HCl in EtOH (68 mL) was added slowly. The resulting precipitate was filtered, washed with water and ether, and the residue was dried on a high vacuum overnight to afford the title compound (8.9 g, crude) as a pink solid. MW=192.26. 1H NMR (DMSO-d6, 500 MHz) δ 12.00 (s, 1H), 6.14 (s, 1H), 3.01 (quin, J=8.0 Hz, 1H), 2.55 (q, J=7.5 Hz, 2H), 2.13-2.01 (m, 2H), 1.94-1.77 (m, 4H), 1.74-1.63 (m, 2H), 1.22 (t, J=7.5 Hz, 3H); APCI MS m/z 193 [M+H]+.

1. temperatureAfter this time, the mixture was cooled
2. concentrationconcentrated to a volume of approximately 50 mL
3. additionThen, 2M HCl in EtOH (68 mL) was added slowly
4. filtrationThe resulting precipitate was filtered
5. washwashed with water and ether
6. customthe residue was dried on a high vacuum overnight

ORD record

ord-2c6b09dd64c44289b2bfea8336472c71

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221843B2