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

HRID 1851196Notes

Reaction equation

HRID 1851196 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 were 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 was heated to 120° C. by microwave irradiation under an inert gas atmosphere for 1 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 evaporated. The crude product was 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 were dried over sodium sulphate
  4. customevaporated
  5. customThe crude product was purified by silica gel chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-ce862d97d2d34e1888c257b547dfa79e
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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