4-Chloro-2-hydroxypyridine

Step 1; To a solution of A solution of General procedure: To a suspension of an appropriate heterocyclic base (1mmol) in 2mLof acetonitrile, 243 muL (1mmol)ofBSAwas added. Inthe case of synthesisof compounds 12 and 15, 2 mmol of BSA were added. The reaction mixture was stirred at room temperaturefor 40 min, and 260 mg (1 mmol) of 1, 3, 5-tri-O-acetyl-D-ribose was dissolved in0.5 mL of acetonitrile, and 117 muL (1mmol) of SnCl4 was added. The reaction mixturewas stirred at room temperature overnight. The reaction mixture of protectednucleosides with halogen and hydrogen atoms at the 4th position of heterocyclicbase (11, 13, and 14) was dissolved in 60 mL of ethyl acetate and washed for fivetimes with saturated NaHCO3 solution. The organic phase was dried (Na2SO4) andevaporated under reduced pressure. The residuewas purified by column chromatography(silica gel, chloroform/methanol mixture, 10:0'10:0.5). The crude reactionmixture of protected nucleosides with hydroxyl and carboxyl groups of heterocyclicbase (12 and 15) was concentrated under reduced pressure and dissolved in 2 mLof methanol/water, 3/1 solution. The precipitate was filtered and washed twice with1 mL of methanol/water, 3/1 solution. The filtrate was concentrated under reducedpressure, the residue was dissolved in water (1 mL) and purified by reverse phasecolumn chromatography (C-18 cartridges, methanol/water mixture, 10:0'10:4).The solvents were removed under reduced pressure to afford colorless oil reactionproducts 11-15.

Molecular Weight:129.54
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:128.9981414
Monoisotopic Mass:128.9981414
Topological Polar Surface Area:29.1
Heavy Atom Count:8
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes