Water → 5-(4-Aminophenyl)-6-methylthieno[2,3-d]pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

A suspension of Example 1D (1.01 g, 3.53 mmol) in ethanol (60 mL), THF (20 mL), and water (10 mL) was treated with NH4Cl (0.19 g, 3.53 mmol) and iron powder (1.18 g, 21.2 mmol), and stirred at 70-80° C. for 1 hour. The mixture was diluted with ethanol (40 mL) and filtered through a pad of diatomaceous earth (Celite®) while still hot. The pad was washed with ethanol and the filtrate was concentrated. The concentrate was diluted with water and extracted three times with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide 1 g of the desired product. MS (CI) m/e 257 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.23 (s, 1H); 7.01 (d, J=8.4 Hz, 2H); 6.70 (d, J=8.4 Hz, 2H); 5.39 (s, 2H); 2.27 (s, 3H); Anal. Calcd. for C13H12N4S.0.2C4H8O2.0.2H2O: C, 59.72; H, 5.08; N, 20.19. Found: 59.64; H, 4.99; N, 20.22.

Provenance & Evidence