ChemicalBook CAS DataBase List 2'-O-methyl-2-thiouridine

2'-O-methyl-2-thiouridine synthesis

7synthesis methods

Product Name:2'-O-methyl-2-thiouridine
CAS Number:113886-72-9
Molecular formula:C10H14N2O5S
Molecular Weight:274.29

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Yield:-

Reaction Conditions:

with pyridine;hydrogen sulfide at -50 - 70; for 28 h;Sealed tube;

Steps:

46 Synthesis of 2 -0-Methyl-2-thiouridine (00901073008):

A solution of compound 133 (1 .7 g, 5.94 mmol) in 500 ml_ of anhydrous pyridine in a high-pressure bump vessel was cooled to -50 °C. The in house prepared and dried hydrogen sulfide gas was bubbled in the solution to make it saturated at low temperature. The high-pressure bump was sealed, and heated in an oil bath to 50 °C for 4 h, and then increased to 70 °C for 24 h. The reaction vessel was cooled to room temperature, and allowed to open to the air slowly. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash chromatography on a silica gel column providing desired final product 134 with 98.79% HPLC purity (some starting material was recovered). It was characterized by NMR, MS and UV. ¹ H NMR (DMSO-ay δ 12.66 (s,1 H), 8.20 (d, 1 H, J = 8.0 Hz) , 6.60 (d, 1 H, J = 3.2 Hz), 6.00 (d, 1 H, J = 8.4 Hz), 5.28 (d, 1 H, J = 4.8 Hz), 5.17 (d, 1 H, J = 6.0 Hz), 4.10 (t, 1 H, J = 5.2 Hz), 3.90 (d, 1 H, J = 3.2 Hz), 3.80 (d, 1 H, J = 4.4 Hz), 3.75 (d, 1 H , J = 4.0 Hz), 3.62 (d, 1 H, J = 4.0 Hz), 3.45 (s, 3H) ; Mass Spectrum : m/z 275 (M + H)⁺; 297 (M+Na)⁺.

References:

WO2014/93924,2014,A1 Location in patent:Page/Page column 283; 284

75-09-2 Synthesis