Sodium Carbonate → 4-(5-Methylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde

HRID 1851174Notes

Reaction equation

HRID 1851174 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([NH:14][CH3:15])[N:5]2[CH:16]=[CH:17][N:18]=[C:4]2[N:3]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][NH:14][C:6]1[N:5]2[CH:16]=[CH:17][N:18]=[C:4]2[N:3]=[C:2]([C:24]2[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=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 866306607-chloro-N-methyl-6-phenylimidazo[1,2-a]pyrimidin-5-amine

Product 1

HCID 866306614-(5-Methylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 550 mg of the product of step 1 and 350 mg 4-formylphenylboronic acid in 10 mL 1,2-dimethoxyethane, 55 mg tetrakis (triphenylphosphine) palladium(0) and 4 mL of a 10% w/w sodium carbonate solution were added and the resulting mixture was heated by microwave for 2 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 residue was suspended in ethyl acetate and the resulting mixture was stirred for 2 h at room temperature. The product was collected by filtration and used without further purification.

Workup

  1. additionwere added
  2. temperaturethe resulting mixture was heated by microwave for 2 h
  3. customseparating
  4. extractionthe phases and extraction of the aqueous phase with dichloromethane
  5. dry with materialThe combined organic layers were dried over sodium sulphate
  6. customevaporated
  7. filtrationThe product was collected by filtration
  8. customused without further purification

Sources & evidence

ORD record
ord-62c9fede06cf4b7ab184c072acd186ea
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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