Methanol → 5-Formyl-2,6-Diamino-3-(2,3,5-trichlorophenyl)pyrazine

Temperature

0 °C

Diisobutylaluminium hydride (1.5 M in toluene) (2.12 ml, 3.18×10−3 mole) was added dropwise at 0° C. under nitrogen to a suspension of 5-Cyano-2,6-Diamino-3-(2,3,5-trichlorophenyl)pyrazine (0.5 g, 1.59×10−3 mole) in dry toluene (70 ml) and the reaction was stirred at 0° C. for 1 hr. A further one equivalent of diisobutylaluminium hydride was then added and the mixture again stirred at 0° C. for 1 hr. Methanol (1 ml) was added carefully at 0° C. under nitrogen to destroy excess hydride and the reaction was warmed to room temperature. Ethyl acetate (100 ml) was added and the solution was washed with 5% citric acid solution (2×100 ml). The organic layer was separated, washed with brine (100 ml), dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo to give the desired product. Yield 0.340 g (67%), N.m.r. (D6DMSO) δ: 7.53 (1H, d), 7.91 (1H, d), 6.90-7.80 (4H, b), 9.49 (1H, s).

1. stirringthe mixture again stirred at 0° C. for 1 hr
2. customto destroy excess hydride
3. temperaturethe reaction was warmed to room temperature
4. additionEthyl acetate (100 ml) was added
5. washthe solution was washed with 5% citric acid solution (2×100 ml)
6. customThe organic layer was separated
7. washwashed with brine (100 ml)
8. dry with materialdried over magnesium sulphate
9. filtrationfiltered
10. customthe filtrate evaporated in vacuo

ORD record

ord-cb2372b62b71475682a00f66af537929

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06599905B2