HCID 58166476, compound → HCID 178484257, compound

Participants

Reaction Steps

Zinc chloride (1.24 g, 9.12 mmol) was added to a mixture of the formamidine product from Step 2 (0.656 g, 2.28 mmol) in absolute EtOH (10 mL). The resultant mixture was heated to reflux under N2. The mixture gradually turned into a light yellow, homogeneous solution. After refluxing for 90 min a precipitate had formed, and after 2 h, the reaction mixture was allowed to cool to room temperature and was concentrated in vacuo. The residue was treated with CH2Cl2 (75 mL, slightly turbid in appearance) and washed with H2O (25 mL). As soon as H2O was added a white precipitate formed in both layers in the separatory funnel. The solid was removed by vacuum filtration. The solid was washed with H2O followed by Et2O. After air-drying overnight the white solid (0.58 g) was treated with 1:1 CH2Cl2/MeOH (˜70 mL) and heated to reflux (turbid mixture). The mixture was filtered and the filtrate was concentrated in vacuo. The residual solid was slurried with hexanes/Et2O (˜3:1) and isolated by vacuum filtration, air-dried and then vacuum oven dried (70-80° C.) to give N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (0.417 g, 78%) as a white powder: mp 291-293° C. dec; 1H NMR (300 MHz, DMSO-d6) δ 8.03 (d, J=6.9 Hz, 1H), 7.62 (br s, 1H), 7.40 (br s, 1H), 7.17 (d, J=7.8 Hz, 2H), 7.12 (d, J=8.1 Hz, 2H), 4.73 (s, 2H), 2.25 (s, 3H); 13C NMR (150 MHz, DMSO-d6) δ 158.2, 154.8, 137.3, 136.3 (d, J=240 Hz), 135.3, 131.1 (d, J=30.6 Hz), 129.7, 128.3, 51.8, 21.3; ESIMS m/z 234 ([M+H]+), m/z 232 ([M−H]−); IR 3298 (m, br), 3100 (m, br), 1685 (s), 1619 (s), 1518 (s), 1447 (m), 1383 (m), 1343 (w), 1120 (w), 776 (w) cm−1.

Provenance & Evidence