Thymine → HCID 70513746, compound

HRID 1649119Notes

Reaction equation

HRID 1649119 reaction equation
[CH3:1][Si:2]([CH3:5])([CH3:4])Cl.[CH3:6][C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1>C[Si](N[Si](C)(C)C)(C)C>[CH3:1][Si:2]([C:12]1[NH:11][C:10](=[O:13])[N:9]([Si:2]([CH3:5])([CH3:4])[CH3:1])[C:8](=[O:14])[C:7]=1[CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 1135ThymineHCID 6397Chlorotrimethylsilane

Product 1

HCID 70513746HCID 70513746, compound

Reagents, catalysts & solvents 1

HCID 13838HexamethyldisilazaneSolvent

Procedure

Trimethylchlorosilane (4 ml) was added to a suspension of 5-methyluracil (thymine) (5 g) in hexamethylsilazane (20 ml) followed by refluxing for 5 hours. The resulting ammonium chloride was removed by filtration and the filtrate was evaporated to give bis(trimethylsilyl)-5-methyluracil as oil. To a solution of the oil in dry dichloromethane (10 ml) was added 2-methyl-1,3-dioxolane (15 ml) and then was added dropwise stannic chloride (5 ml). After allowing the mixture to stand at room temperature overnight, it was treated as in Example 10 to give 4.6 g of crystalline 1-[α-(2-hydroxyethoxy)-ethyl]-5-methyluracil.

Workup

  1. temperatureby refluxing for 5 hours
  2. customThe resulting ammonium chloride was removed by filtration
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b536fe21a7214bb693b3febb6e0b6cd9
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

Loading…