4-Aminotetrahydropyran → 5-Methyl-4-(tetrahydropyran-4-yl)-2,4-dihydro[1,2,4]triazol-3-one

Temperature

100 °C

After dissolving 5-methyl-3H-[1,3,4]oxadiazol-2-one (CAS 3069-67-8) (500 mg) in methanol (5 ml), 4-aminotetrahydropyran (1.01 g) was added and the mixture was heated to reflux for 15 hours. The reaction mixture was concentrated under reduced pressure, and then a 1N aqueous solution of sodium hydroxide (5.5 ml) was added to the residue and the mixture Was stirred at 100° C. for 2 hours. After then adding 5N hydrochloric acid (1.1 ml) to the reaction mixture, it was stirred at room temperature for 3 hours. The precipitate was collected by filtration and washed with water and ethyl acetate in that order to obtain the title compound (400 mg).

1. additionwas added
2. temperaturethe mixture was heated
3. temperatureto reflux for 15 hours
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. additiona 1N aqueous solution of sodium hydroxide (5.5 ml) was added to the residue
6. additionAfter then adding 5N hydrochloric acid (1.1 ml) to the reaction mixture, it
7. stirringwas stirred at room temperature for 3 hours
8. filtrationThe precipitate was collected by filtration
9. washwashed with water and ethyl acetate in that order

ORD record

ord-d5505177918c4e67927e54600b11ac7c

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08252810B2