Hydrochloric Acid → HCID 9803112, compound

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Reaction Steps

Part E: 7-(2,4-Dichlorophenyl)-2,5,6-trimethyl-pyrrolo[3,4-d]pyrimidine-4(3H)-one: The compound of part D of Example 1 (0.25 g, 0.764 mmol) was dissolved in dioxane (2.0 mL) and acetonitrile (2.0 mL) and cooled to 15° C. under nitrogen. Dry HCl (gas) was passed through a syringe needle into the reaction mixture over a period of 4 h. TLC(eluent: 10:1 CH2Cl2/methanol) revealed presence of two new spots at Rf=0.27 and 0.46 (faint) along with unreacted starting material spot at Rf=0.80. Stopped bubbling HCl gas at this stage and allowed to stir at room temp. over night. TLC (eluent: 10:1 CH2Cl2/methanol) revealed absence of starting material spot and also the faint spot at Rf=0.46. The only spot noticed was at Rf=0.27 and mass spectrum revealed formation of acetonitrile addition product (M+H=368). The solvent was removed under vacuum, residue was dissolved in 4.0 mL of 1:1 EtOH/water and basified using 28% ammonium hydroxide to pH 9 to 10. Some solid separation was noticed, but extraction of the mixture with ethyl acetate (15 mL) resulted in separation of white solid. Filtered the solid, washed with ethyl acetate, and dried to afford (0.159 g) desired product. Additional 60 mg of product was obtained by extraction of the aq. layer with EtOAc. Overall yield 0.22 g (88% yield, mp>290° C.). Anal. calcd. for C15H13Cl2N3O: C, 55.92; H, 4.089; N,13.04. Found: C, 55.77; H, 3.99; N, 12.80.

Provenance & Evidence