1,2-Dimethylhydrazine dihydrochloride → 6-(N,N'-dimethyl-hydrazino)-N,N'-dipropyl-[1,3,5]triazine-2,4-diamine

温度

60 °C

A mixture of 2-chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV) (2.50 g, 10.88 mmol), N,N′-dimethyl-hydrazine dihydrochloride (2.89 g, 21.76 mmol) and NaOH (2.18 g, 54.40 mmol) in 1,4-dioxane (40 mL) and water (20 mL) was heated at 60° C. for 18 h. The volatiles were removed under reduced pressure. Saturated NaHCO3 solution (100 mL) was added to the residue, the mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (75 mL), brine (75 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 (CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5)) to yield N-(4,6-Bis-propylamino-[1,3,5]triazin-2-yl)-N,N′-dimethyl-hydrazine (1.17 g, 42%). 200 MHz 1H NMR (DMSO-d6, ppm): 6.81-6.44 (2H, m), 5.31 (1H, br s), 3.24-3.08 (4H, m), 3.05 (3H, s), 2.47-2.40 (3H, m), 1.57-1.37 (4H, m), 0.84 (6H, t, J=7.4 Hz). ESI-MS (m/z): 254 [M+H]+.

1. customThe volatiles were removed under reduced pressure
2. additionSaturated NaHCO3 solution (100 mL) was added to the residue
3. extractionthe mixture was extracted with EtOAc (3×50 mL)
4. washThe combined organic extracts were washed with water (75 mL), brine (75 mL)
5. dry with materialdried over Na2SO4
6. customThe solvent was removed under reduced pressure
7. customthe crude product was purified by flash column chromatography
8. washelution (CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5))

ORDレコード

ord-89dce33b835541da805d6779a07dab3c

出典データセット

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09351972B2