Acetic Acid → 2-(2,6-Dimethylphenyl)-4-(3-methoxypropoxy)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80817

反応式

HRID 80817 の反応式
C([N:8]1[CH2:31][CH2:30][C:11]2[N:12]=[C:13]([C:22]3[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:29])[N:14]=[C:15]([O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])[C:10]=2[CH2:9]1)C1C=CC=CC=1.C(O)(=O)C.[H][H].C(=O)(O)[O-].[Na+]>C1COCC1.ClCCl.[OH-].[OH-].[Pd+2].O>[CH3:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:29])[C:22]=1[C:13]1[N:14]=[C:15]([O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])[C:10]2[CH2:9][NH:8][CH2:31][CH2:30][C:11]=2[N:12]=1

参加物

9

反応物 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 712389296-Benzyl-2-(2,6-dimethylphenyl)-4-(3-methoxypropoxy)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 712388462-(2,6-Dimethylphenyl)-4-(3-methoxypropoxy)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

試薬・触媒・溶媒 4

HCID 9942167Palladium hydroxide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6-benzyl-2-(2,6-dimethylphenyl)-4-(3-methoxypropoxy)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (170 mg, 0.41 mmol) in THF (3.5 mL) was added water (0.5 mL) and acetic acid (0.070 mL, 1.22 mmol). The reaction mixture was placed under argon and then charged with 20 mol % Pd(OH)2/C (50% wet, 114 mg, 0.081 mmol). The atmosphere was then replaced with hydrogen gas via a balloon and was permitted to stir for 5 hours. The mixture was then neutralized with saturated aqueous sodium bicarbonate, diluted with dichloromethane and filtered through a pad of Celite®. The eluent was further diluted with dichloromethane and saturated aqueous sodium bicarbonate and the layers were separated. The aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography [7-20% (2 M NH3 in MeOH)/DCM] to furnish 2-(2,6-dimethylphenyl)-4-(3-methoxypropoxy)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 328.3 (M+H)+.

後処理

  1. filtrationfiltered through a pad of Celite®
  2. additionThe eluent was further diluted with dichloromethane and saturated aqueous sodium bicarbonate
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted two additional times with dichloromethane
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel flash chromatography [7-20% (2 M NH3 in MeOH)/DCM]

出典と根拠

ORDレコード
ord-931cabe046c84d83af253be4af196bae
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

関連ノート

読み込み中…