Guanidine Hydrochloride → 4'-(Cyclopropylmethyl)-2-(methylthio)-4,5'-bipyrimidin-2'-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of (Z)-1-cyclopropyl-4-(dimethylamino)-3-(2-(methylthio)pyrimidin-4-yl)but-3-en-2-one (3) (2.07 g, 7.46 mmol) in DMF (62.2 ml) was added potassium carbonate (3.09 g, 22.39 mmol) and guanidine hydrochloride (1.065 g, 11.19 mmol). The resulting suspension was stirred at 120° C. After 45 minutes, the reaction was complete. The reaction mixture was concentrated in vacuo, then was taken up in EtOAc. The organic solution was washed with water, followed by brine, dried over sodium sulfate, then concentrated in vacuo. The crude residue was dried over high vacuum for 18 h to obtain the desired product as a bright orange product (2.17 g, quant. yield). MS (ES+): m/z=250.1 (50) [MH+]. HPLC: tR=1.13 min over 3 min. Purity: 100% [HPLC (LC/MS) at 220 nm]. 1H NMR (400 MHz, DMSO-d6) d ppm 0.06-0.13 (m, 2H) 0.33-0.41 (m, 2H) 0.96-1.11 (m, 1H) 2.52-2.57 (m, 3H) 2.79 (d, J=7.07 Hz, 2H) 7.03 (s, 2H) 7.39 (d, J=5.56 Hz, 1H) 8.44 (s, 1H) 8.60 (d, J=5.56 Hz, 1H).

Provenance & Evidence