Sodium Carbonate → 1-Benzhydryl-5-phenyl-pyrimidine-2,4-dione

HRID 1486533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1486533
[CH:1]([N:14]1[CH:19]=[C:18](I)[C:17](=[O:21])[NH:16][C:15]1=[O:22])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1(C)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(C)=O.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>[CH:1]([N:14]1[CH:19]=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17](=[O:21])[NH:16][C:15]1=[O:22])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 21863594Toluene ethanolHCID 716549651-Benzhydryl-5-iodo-pyrimidine-2,4-dione

Produkt 1

HCID 900178241-Benzhydryl-5-phenyl-pyrimidine-2,4-dioneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-Benzhydryl-5-iodo-pyrimidine-2,4-dione (0.06 g, 0.15 mmol) was suspended in a 1:1 toluene/ethanol mixture (1,6 Phenylboronic acid (0.03 g, 0.22 mmol) was added followed by 2M aqueous solution of sodium carbonate (0.082 mL, 0.16 mmol). The resulting suspension was degassed under nitrogen atmosphere for 10 min, then tetrakis(triphenylphosphine) palladium(0) (0.017 g, 0.015 mmol) was added. The reaction was heated under microwave irradiation at 100° C. for 30 min. The reaction mixture was diluted with EtOAc and water was added. The two phases were separated and the aqueous layer was extracted with EtOAc (3×15 mL). The combined organic phases were dried over Na2SO4 and the solvent was removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 60:40) to afford the title compound (0.03 g, 62%) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.13 (s, 1H), 7.20-7.24 (m, 5H), 7.25 (s, 1H), 7.32-7.35 (m, 5H), 7.37-7.44 (m, 5H), 8.19 (br s, 1H). MS (ESI) to/z: 355 [M-H]+.

Aufarbeitung

  1. additionwas added
  2. customThe resulting suspension was degassed under nitrogen atmosphere for 10 min
  3. additionwas added
  4. customThe two phases were separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×15 mL)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. customthe solvent was removed under reduced pressure
  8. customThe crude was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-20a472e1d2654df69a3beb3f6f2a7269
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428465B2

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