Pyridine → HCID 15521320, compound

Participants

Reaction Conditions

Reaction Steps

6-Iodo-3H-quinazolin-4-one (50 gm, 18.3 mmol) was slurried in 60 mL methylene chloride (CH2Cl2) with several drops of DMF. Oxalyl chloride (6.99 g, 4.83 mL, 55.1 mmol) was added dropwise to the slurry at 0° C. The reaction was refluxed for 48 hours and then concentrated in vacuo. Pyridine (2.9 gm, 2.97 mL, 36.7 mmol) and tert-butyl alcohol (10 mL) was added to dissolve the 4-chloro-6-iodo quinazoline. 5-Aminoindole (2.9 gm, 22.0 mmol) was added and the reaction was heated to 60° C. overnight. Diluted the reaction mixture with chloroform (CHCl3) and washed with brine, saturated aqueous NaCHO3 and dried over NaSO4. The organic layer was concentrated in vacuo to a black oil. The crude product was chromatographed on silica gel (2 parts methanol to 1 part methylene chloride (2 MeOH/CH2Cl2)) to provide 2.99 gm of white crystalline product.

Provenance & Evidence