Water → HCID 12802681, compound

HRID 1156571Notes

Reaction equation

HRID 1156571 reaction equation
C(O[CH:5]([O:12][CH2:13][O:14][C:15](=[O:17])[CH3:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)C.C[Si](C)(C)[O:20][C:21]1[N:26]=[C:25]([O:27][Si](C)(C)C)[C:24]([F:32])=[CH:23][N:22]=1.C(=O)([O-])O.[Na+].O>C(#N)C>[C:15]([O:14][CH2:13][O:12][CH:5]([N:22]1[CH:23]=[C:24]([F:32])[C:25](=[O:27])[NH:26][C:21]1=[O:20])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 140203O,O'-Bis(trimethylsilyl)-5-fluorouracilHCID 516892Sodium BicarbonateHCID 12802675HCID 12802675, compound

Product 1

HCID 12802681HCID 12802681, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A solution of α-acetoxymethoxybenzyl alcohol acetate (1.43 g; 6 mmoles) prepared in Example I - 1 and 2,4-di-(trimethylsilyloxy)-5-fluoropyrimidine (1.37 g; 5 mmoles) in dry acetonitrile (25 ml) is cooled at 0° C. Stannic chloride (d=2.26; 0.58 ml; 5 mmoles) is added thereto, and the mixture is stirred at 0° C. for 30 minutes, then mixed with sodium hydrogencarbonate (2.52 g; 30 mmoles) and water (2.5 ml), and vigorously stirred at 0° C. The insoluble materials are filtered off and washed with acetonitrile and methylene chloride. The organic layer is washed with an aqueous saturated solution of sodium hydrogencarbonate and then with saturated brine, dried over magnesium sulfate, and evaporated. The residue is chromatographed on a column of silica gel and eluted with benzene-ethyl acetate (2:1). The eluate is recrystallized from ether to give the title compound (0.88 g; yield 57%). mp. 108°-109° C.

Workup

  1. stirringvigorously stirred at 0° C
  2. filtrationThe insoluble materials are filtered off
  3. washwashed with acetonitrile and methylene chloride
  4. washThe organic layer is washed with an aqueous saturated solution of sodium hydrogencarbonate
  5. dry with materialwith saturated brine, dried over magnesium sulfate
  6. customevaporated
  7. customThe residue is chromatographed on a column of silica gel
  8. washeluted with benzene-ethyl acetate (2:1)
  9. customThe eluate is recrystallized from ether

Sources & evidence

ORD record
ord-57adf092a6c347c5bfd44074ae495c29
Source dataset
uspto-grants-1982_06
Patent number
US04336381

Reaction notes

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