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

HRID 237388Notes

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

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

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

Sources & evidence

ORD record: ord-a29a2153f391426a8ac5ea3b61617bdf
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642594B2

Reaction notes

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