Triethylamine → Thymine

HRID 1613134Notes

Reaction equation

HRID 1613134 reaction equation
C(N(CC)CC)C.S(Cl)(C)(=O)=O.[Si](O[C@@H]1[C@@](COS(C)(=O)=O)(CO)O[C@@H]([N:34]2[CH:42]=[C:40]([CH3:41])[C:38](=[O:39])[NH:37][C:35]2=[O:36])C1)(C(C)(C)C)(C)C>C(Cl)Cl>[NH:34]1[CH:42]=[C:40]([CH3:41])[C:38](=[O:39])[NH:37][C:35]1=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18650254HCID 18650254, compound

Product 1

HCID 1135Thymine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
24 °C

Procedure

To a solution of 3'-O-β-butyldimethylsilyl-4'-hydroxymethyl-β-D-erythro-pentofuranosylthymine (1.2 g, 3.1 mM), prepared, e.g., as described in Preparation 4, in CH2Cl2 (20 ml), triethylamine (0.6 g. 6 mM) was added followed by the dropwise addition of mesyl chloride (0.340 g, 3 mM), while the solution was stirred at 24° C. The solution was concentrated by the removal of the solvent by evaporation. The residue was flash chromatographed on silica gel eluting by CH2Cl2 with 5% methanol, to give a mixture of the 4'-α and 4'-β isomers of 3'-O-t-butyldimethylsilyl-4'-methanesulfonyloxymethylthymidine (1.1 g, 2.4 mM). Calcd. for C18H32N2O8Si: C, 46.53; H, 6.94; N, 6.05. Found: C, 46.90; H, 7.02; N, 5.78.

Workup

  1. concentrationThe solution was concentrated by the removal of the solvent by evaporation
  2. customchromatographed on silica gel eluting by CH2Cl2 with 5% methanol
  3. customto give

Sources & evidence

ORD record
ord-d7140cc5c2924ba7b0084dff0a085303
Source dataset
uspto-grants-1993_03
Patent number
US05192749

Reaction notes

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