Acetic Acid → 5-(4-Chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidine

HRID 393742ノート

反応式

HRID 393742 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH:19]=3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.CO.C(O)(=O)C>C(OCC)(=O)C.[Pt](=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([CH:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 887MethanolHCID 226466955-(4-Chlorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine

生成物 1

HCID 226466965-(4-Chlorophenyl)-2-(1-methylpiperidin-4-yl)pyrimidine収率 45%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 8857Ethyl Acetate溶媒

実験手順

Platinum(IV) oxide (30 mg) was added to a solution of 5-(4-chlorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin -4-yl)pyrimidine (0.31 g) in a mixture of ethyl acetate (20 ml), methanol (3 ml) and acetic acid (1 ml) and the mixture was hydrogenated at atmospheric pressure for 18 h. The mixture was then filtered through celite, washing with 10% methanol/ethyl acetate, and evaporated under reduced pressure. The residue was treated with 2 M sodium hydroxide (15 ml) and extracted with diethyl ether (2×25 ml), and the organic extracts were washed with water (2×10 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure and the residue purified by silica gel column chromatography with 10% methanol/dichloromethane with 0.5% concentrated aqueous ammonia as eluent, to yield the title compound as a white solid (0.14 g, 45%).

後処理

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with 10% methanol/ethyl acetate
  3. customevaporated under reduced pressure
  4. additionThe residue was treated with 2 M sodium hydroxide (15 ml)
  5. extractionextracted with diethyl ether (2×25 ml)
  6. washthe organic extracts were washed with water (2×10 ml), saturated brine (20 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customthe residue purified by silica gel column chromatography with 10% methanol/dichloromethane with 0.5% concentrated aqueous ammonia as eluent

出典と根拠

ORDレコード
ord-ceb51a803c5445b7ae77ac2c5c6d8e76
出典データセット
uspto-grants-2004_10
特許番号
US06809100B2

反応ノート

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