Imidazole → HCID 22808836, compound

HRID 1732911Notes

Reaction equation

HRID 1732911 reaction equation
[C@@H:1]1([N:9]2[CH2:14][N:13]([CH3:15])[C:12](=[O:16])[NH:11][C:10]2=[O:17])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.CN(C)C=O.N1C=CN=C1.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>O.C(Cl)(Cl)Cl>[Si:28]([CH:7]([OH:8])[C@H:5]1[O:6][C@@H:1]([N:9]2[CH2:14][N:13]([CH3:15])[C:12](=[O:16])[NH:11][C:10]2=[O:17])[CH2:2][C@@H:3]1[OH:4])([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 795Imidazole2×HCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 13248214HCID 13248214, compound

Product 1

HCID 22808836HCID 22808836, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A reaction mixture consisting of 12.25 gm. (0.050 mole) of 1-(2-deoxy-β-D-ribofuranosyl)-5,6-dihydro-5-methyl-s-triazine-2,4-(1H,3H)-dione, 50 ml. dimethylformamide, and 8.5 gm. (0.125 mole) of imidazole was warmed to 35° C. and stirred until the imidazole had dissolved. There was then added with continued stirring 7.55 gm. (0.050 mole) tert-butyldimethylsilyl chloride. Stirring was continued for 18 hours at 35° C. The solvent medium was then removed by evaporation under reduced pressure, and the residue thus obtained was dispersed in a solvent mixture consisting of 200 ml. chloroform and 50 ml. water. The two phases were allowed to stabilize and the aqueous phase was recovered. It was washed two times with 50 ml. portions of chloroform. The three chloroform layers (original and two washings) were combined and washed with three-25 ml. portions of water. The washed chloroform solution was dried over anhydrous magnesium sulfate and filtered. The chloroform was then removed by evaporation under reduced pressure to give 14.8 gm. (82.5% yield) of 1-(5-tert-butyldimethylsilyl-2-deoxy-β-D-ribofuranosyl)5,6-dihydro-5-methyl-s-triazine-2,4-(1H,3H)-dione.

Workup

  1. dissolutionhad dissolved
  2. additionThere was then added
  3. stirringStirring
  4. customThe solvent medium was then removed by evaporation under reduced pressure
  5. customthe residue thus obtained
  6. additionwas dispersed in a solvent mixture
  7. customthe aqueous phase was recovered
  8. washIt was washed two times with 50 ml
  9. washwashed with three-25 ml
  10. dry with materialThe washed chloroform solution was dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customThe chloroform was then removed by evaporation under reduced pressure
  13. customto give 14.8 gm

Sources & evidence

ORD record
ord-7aef25582eda44cd98a2fdd2315cec7c
Source dataset
uspto-grants-1980_12
Patent number
US04239753

Reaction notes

Loading…