Methanethiol → 2'-Deoxy-2'-methylthio-5-methyluridine

HRID 381692

Reaction equation

HRID 381692 reaction equation
[CH3:1][C:2]1[C:16](=[O:17])[N:15]=[C:14]2[N:4]([C@@H:5]3[O:9][C@H:8]([CH2:10][OH:11])[C@@H:7]([OH:12])[C@@H:6]3[O:13]2)[CH:3]=1.[CH3:18][SH:19].CN(C)C(N(C)C)=N>CN(C)C=O>[CH3:18][S:19][C@@H:6]1[C@H:7]([OH:12])[C@@H:8]([CH2:10][OH:11])[O:9][C@H:5]1[N:4]1[CH:3]=[C:2]([CH3:1])[C:16](=[O:17])[NH:15][C:14]1=[O:13]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 664601,1,3,3-TetramethylguanidineHCID 1680452,2'-Anhydro-1-beta-arabinofuranosylthymine

Product 1

HCID 103342932'-Deoxy-2'-methylthio-5-methyluridineYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.2′-Anhydro-5-methyluridine (17.02 g, 70.6 mmol), methanethiol (16.3 g, 339 mmol), 1,1,3,3-tetramethylguanidine (40.6 g, 353 mmol), and dimethylformamide (150 ml) were heated together at 60° C. After 12 hr, the products were cooled and concentrated under reduced pressure. The residual oil was purified by short silica gel (300 g) column chromatography. Concentration of appropriate fractions, which were eluted with CH2Cl2-MeOH (93:7, v/v), furnished the title compound as a white foam (15.08 g, 74.1%). Crystallization from EtOH-CH2Cl2 furnished white needles.

Workup

  1. temperaturethe products were cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residual oil was purified by short silica gel (300 g) column chromatography
  4. washConcentration of appropriate fractions, which were eluted with CH2Cl2-MeOH (93:7

Sources & evidence

ORD record
ord-6b367e86d8654ac4a8f7118bd2a4d660
Source dataset
uspto-grants-2001_10
Patent number
US06307040B1

Linked notes

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