Process for preparing N.sub.1 -(2'-furanidyl)-5-fluorouracil

• US 4,107,162 A
• Filed: 11/09/1976
• Issued: 08/15/1978
• Est. Priority Date: 11/10/1975
• Status: Expired due to Term

• Current Assignee: Asahi Kasei Kogyo Kabushiki Kaisha (Asahi Kasei Corporation)
• Original Assignee: Asahi Kasei Kogyo Kabushiki Kaisha (Asahi Kasei Corporation)
• Inventors: Takagi, Seiji, Sone, Takanori, Wakabayashi, Mikio, Suzuki, Nobuyuki, Kobayashi, Yukinari, Hiyoshi, Yumiko, Sowa, Tuneo
• Primary Examiner(s): Coughlan, Jr., Paul M.
• Application Number:
  US05/740,324
• Time in Patent Office: 644 Days
• Field of Search: 260/260
• US Class Current: 544/313
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond

Abstract

Process for preparing N₁ -(2'"'"'-furanidyl)-5-fluorouracil having effective pharmacological activities such as anti-leukemia and anti-tumor activities comprising reacting 2,4-bis(trialkylsilyl)-5-fluorouracil with 2,3-dihydrofuran in the presence of a proton donor and a catalyst. Such process can be simply, easily conducted to give the desired product having a high purity in good yield.

Claims

1. A process for preparing N₁ -(2'"'"'-furanidyl)-5-fluorouracil of the formula ##STR6## which comprises reacting a 2,4-bis(trialkylsilyl)-5-fluorouracil of the formula ##STR7## wherein R is a lower alkyl group, with 2,3-dihydrofuran in the presence of a catalyst selected from the group consisting of stannic chloride, aluminum chloride, titanium tetrachloride, silicon tetrachloride, antimony pentachloride, boron trifluoride, bromine, iodine, lithium iodide, sodium iodide, potassium iodide and mixtures thereof and a proton donor selected from the group consisting of water, an alcohol, an organic acid and mixtures thereof.

2. A process as claimed in Claim 1, wherein said lower alkyl group is a member selected from the group consisting of methyl and ethyl.

3. a process as claimed in claim 1, wherein 2,3-dihydrofuran is employed in an amount of 0.8 to 2.0 moles per mole of the compound of the formula (II).

4. A process as claimed in claim 1, wherein said catalyst is employed in an amount of 0.1 to 50 mole %, based on the compound of the formula (II).

5. A process as claimed in claim 1, wherein said proton donor is a member selected from the group consisting of methanol, ethanol, propanol, butanol and mixtures thereof.

6. A process as claimed in claim 1, wherein said proton donor is a member selected from the group consisting of acetic acid, propionic acid, methanesulfonic acid and mixtures thereof.

7. A process as claimed in claim 1, wherein said proton donor is employed in an amount of 0.1 to 2.0 moles per mole of the compound of the formula (II).

8. A process as claimed in claim 1, wherein the reaction is effected at a temperature of 10°

to 200°

C.

9. A process as claimed in claim 1, wherein the reaction is effected for 20 minutes to 15 hours.