2,4-Dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

A 50-L jacketed reactor was charged with 2, 4-dichloro-7H-pyrrolo[2, 3-d]pyrimidine (950 g, 5053 mmol) and DCM (16 L). The resulting tan suspension was cooled to 16° C., and N-iodosuccinimide (1598 g, 7104 mmol) was added portionwise over 20 min. The reaction mixture was stirred at room temperature for 16 h, after which time TLC analysis (2:1 hexane/ethyl acetate) indicated complete reaction. The resulting precipitate was filtered, washed with DCM (3×1.5 L), and dried under reduced pressure at 40° C. for 64 h to afford 1447 g (Yield: 91percent) of target compound as a beige solid. MS (ESI) m/z 314.0 [M+1]To a suspension of 2.4-dichloro-7H--pvrro]o[2, 3-dipyrimidine (7.2 g, 38 rnmoi) in DCM (120 mL) was added N4odosuccinimide (12.0 g. 53.3 rnmol) in portions over 30 mm. The mixture was stirred at 25 °C for 16 h. The mixture was filtered, the filtered cake was washed with DCM to give 2, 4-dichioro-5-iodo--7H-pyrroio[2, 3-d]pyrimidine (131a) (76 g, 24 mmoi, 64percent yield) as a white solid. LCMS [M-FF{]: 3139.To a stirred solution of 2, 4-dichloro-7H-pyrrrolo[2, 3-(f]pyrimidine (25 g) in DMF (100 mL) was charged N-Iodosuccinamide (31.41g). The reaction mixture was stirred for 3-4 h at ambient temperature and poured into water. Precipitates were filtered and washed with water (500 mL). Filtered solid was suck dried and extracted into ethylacetate (800 mL) and washed with water (300 mL). Organic layer was dried over anhydrous sodium sulphate and concentrated under vacuum. Trituration of the solid with hexanes (125 mL) followed by filtration and drying afforded an off-white solid (30 g).

Molecular Weight:313.91
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:312.86705
Monoisotopic Mass:312.86705
Topological Polar Surface Area:41.6
Heavy Atom Count:12
Complexity:182
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes