Diethyl allylmalonate → HCID 178439779, compound

Temperature

0 °C

Sodium metal (4.5 g) was added slowly into ethanol (100 mL) in a 500 mL round bottom flask under nitrogen atmosphere. The reaction mixture was stirred at room temperature until all the sodium metal dissolved, before being cooled to 0° C. Diethyl 2-allylmalonate (12 g) was added into the reaction mixture, followed by formamidine acetate (6.24 g) under nitrogen atmosphere at 0° C. The reaction was stirred at room temperature for 24 hours under nitrogen atmosphere, before being quenched by acetic acid (20 mL), followed by water (100 mL). The white precipitate was filtered, washed with water (4×50 mL), methanol (2×50 mL) and dried under vacuum to afford 5-allylpyrimidine-4,6-diol (4 g) as white solid. 1H NMR (DMSO-d6): δ 2.96 (d, 2H), 4.85 (dd, 1H), 4.91 (dd, 1H), 5.76 (dd, 1H), 7.89 (s, 1H), 11.64 (bs, 2H).

1. dissolutiondissolved
2. custombefore being quenched by acetic acid (20 mL)
3. filtrationThe white precipitate was filtered
4. washwashed with water (4×50 mL), methanol (2×50 mL)
5. customdried under vacuum

ORD record

ord-1d6395cdb971418cb3fc949c9bf22885

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193725B2