Acetic Anhydride → 4,6-Bis(1,1-dimethylethyl)-2-[[2-(3-pyridinyl)]ethenyl]-5-pyrimidinol

HRID 1645797

反応式

HRID 1645797 の反応式
[CH3:1][C:2]([C:5]1[C:10]([O:11]COCCOC)=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=[C:7]([CH2:22][CH:23]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)O)[N:6]=1)([CH3:4])[CH3:3].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[CH3:21][C:18]([C:9]1[C:10]([OH:11])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[N:6]=[C:7]([CH:22]=[CH:23][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[N:8]=1)([CH3:19])[CH3:20]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 190071464,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-alpha-(3-pyridinyl)-2-pyrimidine-ethanol

生成物 1

HCID 545666324,6-Bis(1,1-dimethylethyl)-2-[[2-(3-pyridinyl)]ethenyl]-5-pyrimidinol収率 49.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
190 °C

実験手順

A mixture of 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-α-(3-pyridinyl)-2-pyrimidine-ethanol (350 mg), sodium acetate (10 g) and acetic anhydride (7 mL) in toluene (100 mL) is heated at reflux for 8 hours. The reaction mixture is cooled and the solvent is evaporated. Dichlorobenzene (30 mL) is added and the reaction mixture is heated at 190° C. for 30 minutes. The reaction mixture is cooled and partitioned between ethyl acetate and water. The aqueous layer is adjusted to pH 4 with 1 N HCl. The organic layer is collected and evaporated. Purification of the residue by flash chromatography (silica, 1:1 ethyl acetate/hexane) followed by recrystallization from hexane gives pure 4,6-bis(1,1-dimethylethyl)-2-[[2-(3 pyridinyl)]ethenyl]-5-pyrimidinol (130 mg, 40%); mp 150°-151° C.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 8 hours
  3. temperatureThe reaction mixture is cooled
  4. customthe solvent is evaporated
  5. additionDichlorobenzene (30 mL) is added
  6. temperatureThe reaction mixture is cooled
  7. custompartitioned between ethyl acetate and water
  8. customThe organic layer is collected
  9. customevaporated
  10. customPurification of the residue by flash chromatography (silica, 1:1 ethyl acetate/hexane)
  11. customfollowed by recrystallization from hexane

出典と根拠

ORDレコード
ord-80ecaebd6b5d4d8dbdd2a83fe26ae6e6
出典データセット
uspto-grants-1993_01
特許番号
US05177079

関連ノート

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