2-methylsulfanylethanamine;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dried reaction flask, 2-(methylthio)ethylamine hydrochloride (6.382 g, 50.0 mmol) and TEA (triethylamine) (13.9 mL, 100 mmol) were dissolved in tetrahydrofuran (63.3 mL). To the mixture was added dropwise Boc2O(di-tert-butyl dicarbonate) (12.3 g, 56.4 mmol) dissolved in tetrahydrofuran (10 mL) under an ice-salt bath. The mixture was stirred at room temperature for 21 hr. Water and ethyl acetate were added. The mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to produce a crude colorless oil (11.752 g). The mixture was extracted with ethyl acetate The combined organic phase was washed with brine dried over anhydrous sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10.0 g of compound 5-(4-(4-(3-fluorobenzyloxy)-3-chloroanilino)-6-quinazolinyl)furan-2-formaldehyde was dissolved in the mixture of dichloromethane/methanol (3:1). The mixture was added with 4.3 g of triethylamine, stirred for 10 min, added with 6.9 g of 2-methylthioethylamine hydrochloride, and stirred at room temperature. Upon consumption of the starting materials detected by TLC, 2.4 g of sodium borohydride was added in batches under ice-bath. Upon the end of reaction detected by TLC, dichloromethane (q.s.) was added. The mixture was washed with saturated ammonium chloride and then with saturated sodium chloride, dried over anhydrous sodium sulfate, and subjected to a column chromatography to obtain 6.5 g of yellow solid, yield 56%. stirred at room temperature Upon consumption of the starting materials was added in batches under ice-bath Upon the end of reaction was added The mixture was washed with saturated ammonium chloride with saturated sodium chloride, dried over anhydrous sodium sulfate