5-Fluorouracil → Tegafur

HRID 1707164

Reaction equation

HRID 1707164 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C[Si](N[Si](C)(C)C)(C)C.Cl[Sn](Cl)(Cl)Cl.C(O[CH:28]1[CH2:32][CH2:31][CH2:30][O:29]1)(=O)C.COC1CCCO1>C(Cl)CCl>[O:29]1[CH2:30][CH2:31][CH2:32][CH:28]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Participants

7

Reactant 5

HCID 33855-FluorouracilHCID 13838HexamethyldisilazaneHCID 24287Tin tetrachlorideHCID 47519Tetrahydro-2-methoxyfuranHCID 102657Tetrahydro-2-furyl acetate

Product 1

HCID 5386TegafurYield 87%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

0.65 g. (5 mmol) of 5-fluorouracil was agitated in 50 ml. of absolute ethylene chloride for one hour with 0.65 g. (4 mmol) of HMDS, 0.43 g. (4 mmol) of TCS, and 1.56 g. (6 mmol) of SnCl4 ; then 0.65 g. (5 mmol) of 2-acetoxytetrahydrofuran or 0.51 g. (5 mmol) of 2-methoxytetrahydrofuran was added to the mixture, and the latter was agitated for 2 hours and 4 hours, respectively, at 24° C. The mixture was worked up as described in Example 1, giving in an 87% yield N1 -(2-tetrahydrofuryl)-5-fluorouracil, m.p. 165°-167° C.

Workup

  1. customat 24° C

Sources & evidence

ORD record
ord-9070a9e3beac4190a465513a1d707e4b
Source dataset
uspto-grants-1980_06
Patent number
US04209613

Linked notes

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