but-3-enyl carbonochloridate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2-methyl-2-thiopseudourea sulfate (12 g, 278 mmol) and potassium carbonate (12 g, 138 mmol) in toluene (50 ml) and water (50 ml) at 25° C. was added but-3-en-1-yl chloroformate (3.0 g, 134 mmol) then stirred for 2.5 h. The biphasic reaction mixture was separated, and the organic phase was washed with water (2×80 ml), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to afford but-3-en-1-yl[imino(methylthio)methyl]carbamate (4.0 g, 96%). MS (EI) for C7H12N2O2S: 287 (MH+). The biphasic reaction mixture was separated the organic phase was washed with water (2×80 ml) dried over anhydrous sodium sulfate filtered The filtrate was concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2-methyl-2-thiopseudourea sulfate (12 g, 278 mmol) and potassium carbonate (12 g, 138 mmol) in toluene (50 ml) and water (50 ml) at 25° C. was added but-3-en-1-yl chloroformate (3.0 g, 134 mmol) then stirred for 2.5 h. The biphasic reaction mixture was separated, and the organic phase was washed with water (2×80 ml), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to afford but-3-en-1-yl[imino(methylthio)methyl]carbamate (4.0 g, 96%). MS (EI) for C7H12N2O2S: 287 (MH+). The biphasic reaction mixture was separated the organic phase was washed with water (2×80 ml) dried over anhydrous sodium sulfate filtered The filtrate was concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2-methyl-2-thiopseudourea sulfate (12 g, 278 mmol) and potassium carbonate (12 g, 138 mmol) in toluene (50 ml) and water (50 ml) at 25° C. was added but-3-en-1-yl chloroformate (3.0 g, 134 mmol) then stirred for 2.5 h. The biphasic reaction mixture was separated, and the organic phase was washed with water (2×80 ml), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to afford but-3-en-1-yl[imino(methylthio)methyl]carbamate (4.0 g, 96%). MS (EI) for C7H12N2O2S: 287 (MH+). The biphasic reaction mixture was separated the organic phase was washed with water (2×80 ml) dried over anhydrous sodium sulfate filtered The filtrate was concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-ylamine (100 mg, 0.46 mmol) in pyridine (3 mL) was added 3-butenyl chloroformate (68 μL, 74 mg, 0.55 mmol). The mixture was stirred at room temperature for 16 h. Ammonium chloride solution was added (50 mL) and the product was extracted with CH2Cl2 (3×50 mL). The organic extracts were combined, dried, filtered, and concentrated under vacuum to give a yellow solid. Crystallisation from EtOAc afforded the pure title product as yellow crystals (122 mg, 84%): mp 204° C. (dec). Anal. RP-HPLC: tR 14.1 min (0-60% MeCN, purity 100%). 1H-NMR (CDCl3): δ 8.36 (s, 1H, Py-H), 7.49 (brs, 1H, NH), 5.90-5.75 (m, 1H, CH), 5.19-5.07 (m, 2H, CH2), 4.27 (t, 2H, J 6.6, CH2), 3.06 (m, 4H, CH2—CH2), 2.77 (s, 3H, CH3), 2.45 (m, 2H, CH2). MS (ESI+): m/z 339.00 (M+Na)+. the product was extracted with CH2Cl2 (3×50 mL) dried filtered concentrated under vacuum to give a yellow solid Crystallisation from EtOAc