Dichloromethane → 2-Amino-4-chloro-6-(2,4-dimethyl-phenyl)-pyrimidine-5-carbaldehyde

HRID 237388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237388
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1B(O)O.[NH2:20][C:21]1[N:26]=[C:25](Cl)[C:24]([CH:28]=[O:29])=[C:23]([Cl:30])[N:22]=1.ClCCl>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[NH2:20][C:21]1[N:22]=[C:23]([Cl:30])[C:24]([CH:28]=[O:29])=[C:25]([C:11]2[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=2[CH3:9])[N:26]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 2655462-Amino-4,6-dichloropyrimidine-5-carboxaldehydeHCID 4198739(2,4-Dimethylphenyl)boronic acid

Produkt 1

HCID 595192012-Amino-4-chloro-6-(2,4-dimethyl-phenyl)-pyrimidine-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Aqueous potassium phosphate was added to a suspension of 2,4-dimethylbenzene boronic acid and 2-amino-4,6-dichloro-5-pyrimidinecarbaldehyde (3 eq) in 1,4-dioxan, under a nitrogen atmosphere. Dichloro bis(triphenylphosphine)palladium (II) (cat.) was added and the mixture heated, ˜100° C., for ˜90 mins. The resulting mixture was allowed to cool and dichloromethane added, the mixture was washed with water and saturated aqueous sodium chloride solution. The solution was dried over anhydrous sodium sulphate and concentrated to a pale yellow solid. The crude solid was purified by column chromatography on silica eluting with mixtures of diethyl ether and hexane.

Aufarbeitung

  1. temperatureto cool
  2. washthe mixture was washed with water and saturated aqueous sodium chloride solution
  3. dry with materialThe solution was dried over anhydrous sodium sulphate
  4. concentrationconcentrated to a pale yellow solid
  5. customThe crude solid was purified by column chromatography on silica eluting with mixtures of diethyl ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-a29a2153f391426a8ac5ea3b61617bdf
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642594B2

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