Water → Tegafur

HRID 46667

Reaction equation

HRID 46667 reaction equation
O.[CH2:2]1[CH2:6][O:5][CH:4]([N:7]2[C:13](=[O:14])[NH:12][C:10](=[O:11])[C:9]([F:15])=[CH:8]2)[CH2:3]1.B(F)(F)F.CCOCC>O1CCOCC1>[F:15][C:9]1[C:10](=[O:11])[NH:12][C:13](=[O:14])[NH:7][CH:8]=1.[CH2:2]1[CH2:6][O:5][CH:4]([N:7]2[C:13](=[O:14])[NH:12][C:10](=[O:11])[C:9]([F:15])=[CH:8]2)[CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 5386TegafurHCID 8000Boron trifluoride etherate

Product 2

HCID 33855-FluorouracilHCID 5386TegafurYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.600 g crude addition product of water to 2,3-dihydrofuran (prepared as described in Example 1) was added under stirring to a mixture of borontrifluoride-etherate (0.710 g; 5.0 m.mole) and anhydrous dioxane (20 ml) followed by the addition of silylated-5-fluorouracil (2,740 g; 10.0 m.mole). The reaction mixture was stirred for 3 hours at room temperature after which it was worked up as described in Example 1. 0.200 g unreacted 5-fluorouracil and 1.580 g (93%) Ftorafur were isolated.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-7db13f0669c74dfcbb795e8755d87758
Source dataset
uspto-grants-1979_11
Patent number
US04174446

Linked notes

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