Sodium Carbonate → 4-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

HRID 1851159Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:14]=[C:15]([CH3:17])[N:16]=[C:4]2[N:3]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:17][C:15]1[N:16]=[C:4]2[N:3]=[C:2]([C:23]3[CH:24]=[CH:25][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=3)[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][N:5]2[N:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 6.90 g 5-chloro-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine and 4.65 g 4-formylphenylboronic acid in 100 mL 1,2-dimethoxyethane were added 55 mL of a 10% w/w sodium carbonate solution and 1.03 g dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II). The resulting mixture was heated to 90° C. under an inert gas atmosphere for 18 h. The work up was performed by diluting the reaction mixture with water and dichloromethane, separating the phases and extraction of the aqueous phase with dichloromethane. The combined organic layers were dried over sodium sulphate and the solvent was evaporated. The residue was purified by chromatography on silica gel (dichloromethane/methanol) to yield the desired product.

Workup

customseparating
extractionthe phases and extraction of the aqueous phase with dichloromethane
dry with materialThe combined organic layers were dried over sodium sulphate
customthe solvent was evaporated
customThe residue was purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record: ord-2d49ce2bffff491498b03308a30bc52f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957064B2

Reaction notes

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