Ammonium Chloride → 6-amino-1-tert-butyl-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-tert-butyl-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (170 mg 0.494 mmol) was suspended in 4 ml of anhydrous THF and ammonium chloride (80 mg 1.48 mmol) was added. The reaction mixture was cooled to 0° C. and LiN(TMS)2 1M in THF (3 ml, 3 mmol) was added; the reaction was stirred for 2 hours. The solvent was then evaporated to dryness, the residue suspended in water and filtered. The crude was purified via silica gel column chromatography eluting with DCM/MeOH 97/3 to give 1-tert-butyl-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide, 100 mg (65% yield), and 6-amino-1-tert-butyl-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide 10 mg (6%). LC/MS (254 nm) HPLC method 2 Rt 6.07 min. 1H NMR (401 MHz, DMSO-d6) δ 9.49 (s, 1H), 8.42 (d, J=8.54 Hz, 1H), 7.80 (d, J=8.79 Hz, 1H), 7.75 (br. s., 1H), 7.53 (br. s., 1H), 2.74 (s, 3H), 2.00 (s, 9H). HRMS (ESI) calcd for C15H17N5OS [M+H]+ 316.1227 found 316.1224.

Provenance & Evidence