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

HRID 80817

Reaktionsgleichung

Reaktionsgleichung von HRID 80817
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

Komponenten

9

Edukt 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, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9942167Palladium hydroxideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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]

Quellen und Nachweise

ORD-Eintrag
ord-931cabe046c84d83af253be4af196bae
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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