Uridine → Uracil Arabinoside

HRID 1050275Notes

Reaction equation

HRID 1050275 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]1[OH:3].C(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.CN(C)P(=O)(N(C)C)N(C)C>C([O-])(O)=O.[Na+].O>[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]1[OH:3]

Participants

6

Reactant 3

HCID 6029UridineHCID 7597Diphenyl carbonateHCID 12679Hexamethylphosphoramide

Product 1

HCID 18323Uracil ArabinosideYield 84%

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of uridine (14; 13.25 g, 54.5 mmol), diphenyl carbonate (15.48 g, 72.5 mmol), anhydrous NaHCO3 (349 mg, 4.15 mmol), and hexamethylphosphoric triamide (50 mL) was heated with stirring at 150° C. under nitrogen for 20 min, and then cooled to room temperature. The mixture was poured into cold water (400 mL), and washed with CHCl3. Et3N (25 mL) was added, and the aqueous solution was heated at 70° C. for 5 h. The solvent was evaporated in vacuo, and the residue was crystallized from MeOH/water to give the title compound 15 as a white solid (11.13 g, 84%). 1H NMR (DMSO-d6) δ 11.2 (s, 1H, NH), 7.60 (d, J=7.5 Hz, 1H, H-6), 5.95 (d, 1H, H-1′), 5.51 (d, J=7.5 Hz, 1H, H-5), 6.30-5.30 (br, 2H, 2 OH), 4.10-3.50 (m, 6H, H-2′, H-3′, H-4′, H-5′, OH).

Workup

  1. temperaturewas heated
  2. temperaturecooled to room temperature
  3. washwashed with CHCl3
  4. additionEt3N (25 mL) was added
  5. temperaturethe aqueous solution was heated at 70° C. for 5 h
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was crystallized from MeOH/water

Sources & evidence

ORD record
ord-07f88134dcb445198acc800640355f87
Source dataset
uspto-grants-2016_07
Patent number
US09382286B2

Reaction notes

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