6-Bromopyrrolo[2,1-F][1,2,4]triazin-4-amine → 6-Methylpyrrolo[2,1-f][1,2,4]triazin-4-amine

Temperatur

90 °C

To a degassed solution of 6-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (Intermediate AAE) (316 mg, 1.48 mmol) and Bis(diphenylphosphino)ferrocenepalladium dichloride (30 mg, 0.037 mmol) in 1,4-dioxane (10 mL), was added dimethyl zinc (2.97 mL, 5.93 mmol, 2.0 M in toluene). The mixture was allowed to stir at 90° C. for 17 hr and then cooled to 0° C. The reaction was quenched with MeOH (1.0 mL) and partitioned between ethyl acetate (200 mL) and potassium phosphate dibasic pH 10 buffer (100 mL). The layers were separated and the organic phase was washed with brine, dried (Na2SO4), and concentrated to dryness. Trituration with Et2O afforded 175 mg (79%) of the desired product. 1H-NMR (DMSO-d6) δ 7.69 (s, 1H), 7.39 (s, 1H), 6.61 (s, 1H), 2.18 (s, 3H); MS [M+H]+=148.9; LCMS RT=1.16.

1. temperaturecooled to 0° C
2. customThe reaction was quenched with MeOH (1.0 mL)
3. custompartitioned between ethyl acetate (200 mL) and potassium phosphate dibasic pH 10 buffer (100 mL)
4. customThe layers were separated
5. washthe organic phase was washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated to dryness

ORD-Eintrag

ord-8917d9b986fb470e8d6cdd572f5cbb8a

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08133995B2