Pyridine → Tegafur

HRID 1112268

反応式

HRID 1112268 の反応式
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.N1[CH:15]=[CH:14][CH:13]=[CH:12]C=1.[O:16]=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[O:30]1[CH:34]=[CH:33][CH2:32][CH2:31]1>CC(C)=O.C(OCC)(=O)C>[O:30]1[CH2:31][CH2:32][CH2:33][CH:34]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[N:4]([CH:12]2[CH2:13][CH2:14][CH2:15][O:16]2)[C:5]1=[O:8].[O:30]1[CH2:34][CH2:33][CH2:32][CH:31]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]

参加物

8

反応物 4

HCID 1049Pyridine2 回HCID 33855-FluorouracilHCID 14812Phosphorus oxide (P4O10)HCID 709342,3-Dihydrofuran

生成物 2

HCID 5386Tegafur収率 63%HCID 1249561,3-Bis(tetrahydro-2-furanyl)-5-fluoro-2,4-pyrimidinedione収率 12.3%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In a sealed tube, 780 mg (6 m mole) of 5-fluorouracil, 5 ml of pyridine, 100 mg (0.70 m mole) of phosphorus pentoxide and 1.26 g (18 m mole) of 2,3-dihydrofuran were heated at 100° C for 17 hours. After the reaction, pyridine was distilled off from the reaction mixture under a reduced pressure. The residue was dissolved in chloroform and the insoluble unreacted 5-fluorouracil was separated by a filtration and the residue was purified by a column chromatography using a silica gel column (mixture of benzene; ethyl acetate and acetone = 2 : 1 : 1 (V/V) as a developing medium) to obtained 200 mg of N1,N3 -bis(2-tetrahydrofuryl)-5-fluorouracil (yield: 12.3%) and 757.6 mg of N1 -(2-tetrahydrofuryl)-5-fluorouracil (yield: 63.0%).

後処理

  1. distillationwas distilled off from the reaction mixture under a reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. customthe insoluble unreacted 5-fluorouracil was separated by a filtration
  4. customthe residue was purified by a column chromatography
  5. additionmixture of benzene

出典と根拠

ORDレコード
ord-54b80a3f12e64822b2b79158c9da1c1a
出典データセット
uspto-grants-1978_10
特許番号
US04121037

関連ノート

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