Sodium Carbonate → 4-(5-Methyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

HRID 503750Notes

Reaction equation

HRID 503750 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([CH3:14])[N:5]2[CH:15]=[CH:16][N:17]=[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]>[CH3:14][C:6]1[N:5]2[CH:15]=[CH:16][N:17]=[C:4]2[N:3]=[C:2]([C:23]2[CH:24]=[CH:25][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 866306677-Chloro-5-methyl-6-phenylimidazo[1,2-a]pyrimidine

Product 1

HCID 866306684-(5-Methyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 220 mg of the product obtained in step 2 and 131 mg 4-formylphenylboronic acid in 10 ml 1,2-dimethoxyethane are added 25 mg dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct and 7 ml of a 10% w/w sodium carbonate solution and the resulting mixture is heated to 120° C. by micro wave irradiation under an inert gas atmosphere for 1 h. The work up is 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 are dried over sodium sulphate and evaporated. The crude product is purified by silica gel chromatography (dichloromethane/methanol).

Workup

  1. customseparating
  2. extractionthe phases and extraction of the aqueous phase with dichloromethane
  3. dry with materialThe combined organic layers are dried over sodium sulphate
  4. customevaporated
  5. customThe crude product is purified by silica gel chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-27b7cd2afade4bd1b384b3f75cebd00a
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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