Carbon Dioxide → 3-Hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-one

HRID 1086146Notes

Reaction equation

HRID 1086146 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1O.CN(C)C=O.C1(OC(=O)OC2C=CC=CC=2)C=CC=CC=1.C(=O)=O>C(=O)(O)[O-].[Na+].CCOCC>[CH:16]1[C:14](=[O:15])[N:13]=[C:11]2[N:10]([CH:1]3[O:9][CH:6]([CH2:7][OH:8])[CH:4]([OH:5])[CH:2]3[O:12]2)[CH:17]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 6029UridineHCID 6228DimethylformamideHCID 7597Diphenyl carbonate

Product 1

HCID 989613-Hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-oneYield 80%

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalystHCID 3283Diethyl EtherSolvent

Procedure

Uridine (10 g, 0.04 mole) was dissolved in 20 ml of warm, dry dimethylformamide, and 11.4 g of diphenylcarbonate (0.06 m) and 0.2 g of sodium bicarbonate were added. The solution was stirred and heated at 150° C. until evolution of carbon dioxide ceased (30 min approx). After cooling the solution was poured into 200 ml of ether with rapid stirring. The resulting solid was filtered off, washed with ether, and recrystallised from methanol to give 7.2 g (80%) of the title compound, as white crystals, melting at 235°-40° C.

Workup

  1. temperatureof warm
  2. custom(30 min approx)
  3. temperatureAfter cooling the solution
  4. filtrationThe resulting solid was filtered off
  5. washwashed with ether
  6. customrecrystallised from methanol

Sources & evidence

ORD record
ord-bbfb7ccb6d8d4097b9633dcd7c1c7d16
Source dataset
uspto-grants-1991_07
Patent number
US05028596

Reaction notes

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