Sodium hydride → (E)-3-[1-Butyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidin-6-yl]prop-2-enal

HRID 1885715ノート

反応式

HRID 1885715 の反応式
C1(NC=CP(=O)(OCC)OCC)CCCCC1.[H-].[Na+].[CH2:20]([N:24]1[C:29]2[N:30]=[C:31]([CH:43]([CH3:45])[CH3:44])[C:32]([CH:41]=O)=[C:33]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[C:28]=2[C:27](=[O:46])[NH:26][C:25]1=[O:47])[CH2:21][CH2:22][CH3:23].O.O.[C:50]([OH:55])(=O)[C:51](O)=O>O1CCCC1.O.C1(C)C=CC=CC=1>[CH2:20]([N:24]1[C:29]2[N:30]=[C:31]([CH:43]([CH3:44])[CH3:45])[C:32](/[CH:41]=[CH:51]/[CH:50]=[O:55])=[C:33]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[C:28]=2[C:27](=[O:46])[NH:26][C:25]1=[O:47])[CH2:21][CH2:22][CH3:23]

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 61373Oxalic acid dihydrateHCID 89268Diethyl [2-(cyclohexylamino)vinyl]phosphonateHCID 198796971-Butyl-5-(4-fluorophenyl)-6-formyl-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidine

生成物 1

HCID 19980383(E)-3-[1-Butyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidin-6-yl]prop-2-enal

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of 1.15 g (4.4 mol) of diethyl 2-(cyclohexylamino)-vinyl-phosphonate in 15 ml of tetrahydrofuran is added dropwise in the course of 10 min at 0°-5° C. under argon to a suspension of 0.25 g (8.4 mmol) of 80% strength sodium hydride in 15 ml of anhydrous tetrahydrofuran. The mixture is stirred at 0° C. for 15 min, a solution of 1.5 g (4 mmol) of the compound from Example 5 in 15 ml of tetrahydrofuran is added dropwise at 0° C. in the course of 20 min, and the mixture is stirred at room temperature for 1 h and under reflux for 20 min. The mixture is cooled, 50 ml of water are added cautiously, the mixture is extracted twice with ethyl acetate, and the combined organic phases are washed with sodium chloride solution and concentrated in vacuo. The residue is heated under reflux with a mixture of 25 ml of toluene, 35 ml of water and 2.6 g (36 mmol) of oxalic acid dihydrate for 1 h. The phases are separated, the aqueous phase is extracted with ethyl acetate, and the combined organic phases are washed with sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The residue is crystallized from ether/petroleum ether.

後処理

  1. stirringthe mixture is stirred at room temperature for 1 h
  2. temperatureunder reflux for 20 min
  3. temperatureThe mixture is cooled
  4. extractionthe mixture is extracted twice with ethyl acetate
  5. washthe combined organic phases are washed with sodium chloride solution
  6. concentrationconcentrated in vacuo
  7. temperatureThe residue is heated
  8. customThe phases are separated
  9. extractionthe aqueous phase is extracted with ethyl acetate
  10. washthe combined organic phases are washed with sodium chloride solution
  11. dry with materialdried over magnesium sulphate
  12. concentrationconcentrated in vacuo
  13. customThe residue is crystallized from ether/petroleum ether

出典と根拠

ORDレコード
ord-3c4093c3d0144d09a6457c66863cbb37
出典データセット
uspto-grants-1992_09
特許番号
US05145959

反応ノート

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