Hydrochloric Acid → HCID 178507154, Verbindung

Beteiligte Stoffe

Reaktionsschritte

4-Amino-3-(4-nitrophenyl)thieno[2,3-d]pyrimidine (11.6 g; 272 g/mole; 42.6 mmoles) was treated with 500 mL HCl 6N and 15 g elemental tin at room temperature. After 15 minutes the reaction was complete by TLC (product has Rf=0.50 in 100% ethyl acetate). The system was placed in an ice bath and treated with concentrated ammonium hydroxide to pH 10 (˜300 mL). At this point, extensive precipitation was observed. Precipitate (A) was collected by filtration and reserved, and the clear solution was treated with 1 L methylene chloride. The aqueous layer was then back-extracted with 3×200 mL methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, and filtered. Precipitate (A), consisting of a mixture of tin salts and product, was extracted with boiling methanol until washings showed no more product by TLC. The resulting solution was combined with the previously reserved organic layers, filtered, concentrated to dryness and dried overnight, generating desired product 4-Amino-3-(4-aminophenyl)thieno[2,3-d]pyrimidine (242 g/mole; nearly quantitative yield), which was recrystallized from methanol.

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