Sodium Carbonate → Methyl[2,6-dimethyl-4-[(2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl)amino]pyrimidin-5-yl]ketone

HRID 129020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129020
[CH3:1][C:2]([C:4]1[C:5]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)=[N:6][C:7]([CH3:11])=[N:8][C:9]=1[CH3:10])=[O:3].[C:21]([N:25]1[C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2B(O)O)=[N:28][N:27]=[N:26]1)([CH3:24])([CH3:23])[CH3:22].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.CCO.CCOC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]([C:4]1[C:5]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[C:29]3[N:25]([C:21]([CH3:24])([CH3:23])[CH3:22])[N:26]=[N:27][N:28]=3)=[CH:16][CH:15]=2)=[N:6][C:7]([CH3:11])=[N:8][C:9]=1[CH3:10])=[O:3]

Komponenten

9

Edukt 3

HCID 10340Sodium CarbonateHCID 10688121Methyl(4-(4-bromobenzylamino)-2,6-dimethylpyrimidin-5-yl)ketoneHCID 109447112-[(1-tert-Butyl)-1H-tetrazol-5-yl]phenylboronic acid

Produkt 1

HCID 11080952Methyl[2,6-dimethyl-4-[(2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl)amino]pyrimidin-5-yl]ketoneAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a heated solution of methyl(4-(4-bromobenzylamino)-2,6-dimethylpyrimidin-5-yl)ketone (1.67 g, 5.00 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.29 g, 0.25 mmol) in toluene (20 mL) was added a partial solution of 2-[(1-tert-butyl)-1H-tetrazol-5-yl]phenylboronic acid (1.50 g, 6.10 mmol) (prepared according to J. W. Ellingboe, et al. U.S. Pat. No. 5,149,699) and Na2CO3 (1.06 g, 10.00 mmol) in water (10 mL) and EtOH (5 mL) in several portions over 1 h. Heating was continued for 2.5 h. The mixture was diluted with EtOAc and the layers were separated. The organic phase was washed with 0.1N NaOH, brine, dried MgSO4) and concentrated. Purification by flash chromatography (40-50% EtOAc/hexane) and trituration with hexane gave 1.71 g (75% ) of product as a white solid. An analytical sample was recrystallized from ether, mp 131°-132° C.

Aufarbeitung

  1. customprepared
  2. temperatureHeating
  3. customthe layers were separated
  4. washThe organic phase was washed with 0.1N NaOH, brine, dried MgSO4) and
  5. concentrationconcentrated
  6. customPurification by flash chromatography (40-50% EtOAc/hexane) and trituration with hexane

Quellen und Nachweise

ORD-Eintrag
ord-ad0afdacb1bd44e8b4c99488789d760a
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466692

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