Hexamethyldisilazane → HCID 67675541, compound

HRID 976942Notes

Reaction equation

HRID 976942 reaction equation
N[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)[NH:5][C:4](=[O:12])[N:3]=1.[CH3:13][Si:14]([CH3:21])([CH3:20])[NH:15][Si](C)(C)C>>[CH3:13][Si:14]([NH:15][N:5]1[C:6]2[C:11](=[N:10][CH:9]=[CH:8][N:7]=2)[CH:2]=[N:3][CH:4]1[O:12][Si:14]([CH3:21])([CH3:20])[CH3:13])([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 13838HexamethyldisilazaneHCID 178509017HCID 178509017, compound

Product 1

HCID 67675541HCID 67675541, compound

Procedure

To 20 mL of hexamethyldisilazane (HMDS) is added 2.98 g (0.02 mole) of 4-amino-pteridine-2-one (30). The mixture is heated for 24 hours under reflux, with moisture excluded, to obtain a clear solution. The excess HMDS is removed under high vacuum to give 1-trimethylsilylamino-2-trimethylsilyloxy-pteridine as a viscous oil. The residue is dissolved in 200 mL of benzene and then 9.37 g (0.022 mole) of 2-deoxy-3,5-di-O-p-toluoyl-α-D-ribofuranosyl chloride, 4 g HgO, and 4 g HgBr2 are added and the mixture is refluxed for 5 hours. After cooling, the precipitate is filtered off, the filtrate evaporated to dryness and the residue dissolved in 100 mL of CHCl3. The solution is extracted twice with 100 mL of 20% KI. The organic layer is then dried over Na2SO4, again evaporated and the residue dissolved in a little ethyl acetate for silica-gel column chromatography with ethyl acetate / acetone 7:3. The first fraction contains excess sugar, the second fraction the α-anomer and last eluting fraction the β-deoxyriboside. Evaporation and recrystallization of the residue from ethanol gives 31.

Workup

  1. temperatureThe mixture is heated for 24 hours
  2. temperatureunder reflux, with moisture
  3. customto obtain a clear solution
  4. customThe excess HMDS is removed under high vacuum

Sources & evidence

ORD record
ord-45328ae826384e27bcd20bfa4199f97b
Source dataset
uspto-grants-1997_03
Patent number
US05612468

Reaction notes

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