Ethyl Acetate → 1,3-dibenzyl-5,6-bis(4-chlorophenyl)pyrimidine-2,4(1H,3H)-dione

HRID 271424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271424
[CH2:1]([N:8]1[C:13](Cl)=[C:12](Br)[C:11](=[O:16])[N:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+].CCO[C:44]([CH3:46])=O>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[C:13]([C:29]2[CH:30]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=2)=[C:12]([C:46]2[CH:44]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=2)[C:11](=[O:16])[N:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 598347971,3-dibenzyl-5-bromo-6-chloropyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 598348061,3-dibenzyl-5,6-bis(4-chlorophenyl)pyrimidine-2,4(1H,3H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 1,3-dibenzyl-5-bromo-6-chloropyrimidine-2,4(1H,3H)-dione (6.0 g, 14.8 mmol) in toluene (50 mL) at room temperature under argon was added 4-chlorophenylboronic acid (7.0 g, 44.77 mmol), tetrakis(triphenylphosphine)palladium (1.03 g, 0.89 mmol), and a solution of Na2CO3 (4.7 g, 44.34 mmol) in water (10 ml). The resulting suspension was stirred at reflux under argon for 6 h. After the reaction mixture was cooled to room temperature, water (50 mL) and EtOAc (75 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluted 15% ethyl acetate-hexanes to obtain 7.2 g of the title compound as a white solid. HPLC/MS (MeOH-water with 10 mM NH4OAc): retention time=4.241 min, [M+H]30 =513.

Aufarbeitung

  1. temperatureat reflux under argon for 6 h
  2. customThe layers were separated
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography
  7. washeluted 15% ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3674e7106a52434baf203497da73df32
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452892B2

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