1-(2-Pyridyl)-2-thiourea → HCID 46700737, compound

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Reaction Steps

According to Scheme 1 Step 4: A solution of 5-bromo-6,7-dihydro-1H-indazol-4(5H)-one (23.3 mmol, 5.00 g) and of 1-(pyridin-2-yl)thiourea (20.9 mmol, 3.21 g) in acetone (60 mL) was stirred at 60° C. for 5 hours. The precipitate formed was filtered and partitioned between AcOEt and a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The organic phase was dried over Na2SO4 and concentrated to yield a grey solid. The crude residue was purified by flash chromatography over silica gel using DCM/MeOH (95:5) as eluent and by two recristallizations with AcOEt/MeOH (50:50) to yield N-(pyridin-2-yl)-5,6-dihydro-4H-thiazolo[4,5-e]indazol-2-amine (11.9 mmol, 3.20 g, 51%) as a white solid.

Provenance & Evidence