5-Allyl-4-chloro-6-(2,4-dichloroanilino)-2-methylpyrimidine → 4-Chloro-1-(2,4-dichlorophenyl)-6-methyl-5,7-diazaindole

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Reaction Steps

Sodium periodate (3.83 g, 17.9 mmol) was added to a stirred solution of (19) (1.94 g, 5.90 mmol) in 3:1 acetone-water (55 mL). The mixture was heated briefly to obtain homogeneity, and a 2.5% solution of osmium tetroxide in t-butanol (0.4 mL) was added. After 20 h, the mixture was diluted with water (50 mL) and saturated sodium thiosulfate (50 mL), and extracted with ethyl acetate. The combined extracts were concentrated under vacuum, and the residue was stirred in dichloromethane (40 mL) and 4 N HCl (5 mL) for 4 h. The mixture was poured into saturated NaHCO3, extracted with dichloromethane, dried (MgSO4), and concentrated in vacuo. The residue was chromatographed (elution with dichloromethane) to afford 0.929 g (50%) of diazaindole (20) as a white solid.

Provenance & Evidence