2-Chloro-5-methylpyrimidine

Step 1 : A suspension of compound 242 (50.0 g, 307 mmol) and freshly activated (acid washed) Zn (59.8 g, 920 mmol) in water (500 mL) was heated at reflux for 3 hours. TLC showed consumption of SM. The reaction mixture was cooled to room temperature, filtered through a pad of celite, and rinsed with CHStep 1.A mixture of 2, 4-dichloro-5-methylpyrimidine (50 g, 0.31 mol), water (500 mL) and zinc dust (50 g, 0.94 mol) was heated at reflux overnight. EXAMPLE 84[4-(6-Bromobenzo[b]thiophen-2-yl)-5-methylpyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine tri-hydrochloride(A). Preparation of 2-chloro-5-methylpyrimidine; Into a 3-necked, 500 mL round bottomed flask is added 2, 4-dichloro-5-methylpyrimidine (25.0 g, 153 mmol), THF (125 mL) and zinc powder (30.1 g, 460 mmol). The mixture is heated to reflux and acetic acid (HOAc) (9.21 g, 153 mmol) in THF (20 mL) is dropwise added over 1 hour. After 1.5 hours at reflux, additional HOAc (3.93 g, 65.5 mmol) in THF (12.5 mL) is added over 10 minutes, and the mixture is refluxed for an additional 1 hour. The mixture is filtered over celite, rinsed with THF (150 mL) and the organic layers are concentrated under reduced pressure. The crude mixture is partitioned in EtOAc/dichloromethane/1 N NaOH and filtered. The organic layer is concentrated under reduced pressure to yield a peach colored solid. The crude material is subjected to chromatography on silica (in hexane) to provide the title compound as a white solid (13.5 g, 69percent yield).A solution of Example 52B (8.8g, 79.9mmol) in phosphorus oxychloride (50mL) was stirred overnight at 90°C.The reaction solution was poured into ice water, and sodium bicarbonate solution was added, the aqueous layer wasextracted with dichloromethane. The organic layer was concentrated to give the title compound (2.8g). 1H NMR (400MHz, DMSO-d6) ppm 2.27 (s, 3 H) 8.64 (s, 2 H).

Molecular Weight:128.56
XLogP3:1.5
Hydrogen Bond Acceptor Count:2
Exact Mass:128.0141259
Monoisotopic Mass:128.0141259
Topological Polar Surface Area:25.8
Heavy Atom Count:8
Complexity:68.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes