2',2'-DIFLUORO-2'-DEOXYURIDINE

Off-White Solid

2',2'-Difluorodeoxyuridine is a pyrimidine 2'-deoxyribonucleoside.

formula 11(5 g, 16.7 mmol, 1.0 eq.) Was dissolved in a 2N aqueous acetic acid solution (350 ml) Sodium nitrite (16.7 g, 14.5 eq.) Was added slowly and left at room temperature for 48 hours. 2N The mixture was adjusted to pH 6-7 with aqueous sodium hydroxide solution and then concentrated under reduced pressure. Decompression concentration After the addition of methanol / ethyl acetate (1: 5, 360 ml), the insoluble salts were removed. This process The salt was removed repeatedly several times to concentrate under reduced pressure to obtain 4.22 g of a light brown transparent oil of formula (7) in 95percent yield.Compound 68-3 was dissolved in NH3/MeOH (600 mL) and stirred overnight. The solvent was concentratedto give the residue, which was purified by silica gel column chromatography (5percent MeOH in DCM) to give68-4 (12 g, 99percent) as a white solidCompound 68-3 was dissolved in NHP24-3 (39.2 g, 83 mmol) was dissolved in saturated methanolic ammonia, and the resulting solution was stirred at R.T. for 15 hours. The solvent was removed, and the residue was purified on a silica gel column (DCM/MeOH=50:1 to 20:1) to give P24-4 (21.0 g, 95.8percent).j0298j Compound P24-3 (39.2 g, 83 mmol) was dissolved in saturated methanolic ammonia, and the resulting solution was stirred at R.T. for 15 hours. The solvent was removed, and the residue was purified on a silica gel column (DCM/MeOH = 50:1 to 20:1) to give P24-4 (21.0 g, 95.8percent).Compound 68-3 was dissolved in NH3/MeOH (600mL) and stirred overnight. The solvent was concentrated togive the residue, which was purified by silica gel columnchromatography (5percent MeOH in DCM) to give 68-4 (12 g, 99percent) as a white solid.

A metabolite of Gemcitabine (G305000) in human plasma.

Molecular Weight:264.18
XLogP3:-1.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:264.05577775
Monoisotopic Mass:264.05577775
Topological Polar Surface Area:99.1
Heavy Atom Count:18
Complexity:414
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes