Sodium Hydroxide → N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-methyl-hydroxylamine

Temperature

60 °C

A mixture of 6-chloro-N,N′-dipropyl-[1,3,5]triazine-2,4-diamine (XXXIV) (2.30 g, 10.01 mmol), O-methyl-hydroxylamine hydrochloride (1.67 g, 20.02 mmol) and NaOH (0.72 g, 18.00 mmol) in 1,4-dioxane (30 mL) and water (6 mL) was heated at 60° C. for 3 h. After this time, NaOH (0.72 g, 18.00 mmol) was added and the reaction mixture was heated for another 3 h. The volatiles were removed under reduced pressure. Saturated NaHCO3 solution (100 mL) was added to the residue, the mixture was extracted with EtOAc (3×25 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography using gradient elution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5) to yield 2.17 g (90%) of N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-methyl-hydroxylamine (XLI). ESI-MS (m/z): 241 [M+H]+

1. temperaturethe reaction mixture was heated for another 3 h
2. customThe volatiles were removed under reduced pressure
3. additionSaturated NaHCO3 solution (100 mL) was added to the residue
4. extractionthe mixture was extracted with EtOAc (3×25 mL)
5. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
6. dry with materialdried over Na2SO4
7. customThe solvent was removed under reduced pressure
8. customthe crude product was purified by flash column chromatography
9. washelution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5)

ORD record

ord-26a0f52df841413993f35d281dbd071d

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09351972B2