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

HRID 1161742Notes

Reaction equation

HRID 1161742 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1aba6cba1ff84ed6acbe5aea29125518
Source dataset
uspto-grants-2010_10
Patent number
US07820658B2

Reaction notes

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