6-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamine → 6-[1,2]oxazinan-2-yl-N,N'-dipropyl-[1,3,5]triazine-2,4-diamine

Temperatur

100 °C

An ACE® pressure tube was charged with 2-chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV) (1.50 g, 6.53 mmol), N-ethyldiisopropylamine (19.59 mmol), 1,2-oxazinane hydrochloride (1.61 g, 13.06 mmol) and tetrahydrofuran. The reaction mixture was heated at 100° C. for 2 h, then cooled and poured into saturated NaHCO3 solution (50 mL). The suspension 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 6-[1,2]oxazinan-2-yl-N,N′-di-n-propyl-[1,3,5]triazine-2,4-diamine (LVII) (1.63 g, 89%). ESI-MS (m/z): 281 [M+H]+.

1. temperaturecooled
2. extractionThe suspension was extracted with EtOAc (3×25 mL)
3. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
4. dry with materialdried over Na2SO4
5. customThe solvent was removed under reduced pressure
6. customthe crude product was purified by flash column chromatography
7. washelution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5)

ORD-Eintrag

ord-e94e45b71a4b4cc4b9e68e165964e2fb

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09162992B2