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

HRID 1851187Notes

Reaction equation

HRID 1851187 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[CH:14]=[C:15]([CH3:17])[N:16]=[C:4]2[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25]>C(COC)OC.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:29]3[CH:30]=[CH:31][C:26]([CH:24]=[O:25])=[CH:27][CH:28]=3)[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][N:5]2[CH:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 866903007-Chloro-2-methyl-6-phenyl-imidazo[1,2-a]pyrimidine

Product 1

HCID 867030344-(2-Methyl-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

2.3 g (9.4 mmol) 7-Chloro-2-methyl 6-phenyl-imidazo[1,2-a]pyrimidine is given in 32 mL dimethoxyethane (not completely dissolved). 18.5 mL Na2CO3 solution (10%) and 1.56 g (10.4 mmol) 4-formylphenylboronic acid are added. After addition of 0.35 g (0.43 mmol) 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) the reaction mixture is purged 3× with argon and heated to 90° C. After 18 h stirring at 90° C. complete dissolution has taken place. The reaction mixture is cooled down and treated with 100 mL water and 150 mL dichloromethane. After vigorous stirring at rt for one hour the organic phase is separated, washed twice with water (100 mL each) and dried (Na2SO4). After removal of the solvent the crude product is purified via chromatography (Isolute, dichloromethane/methanol). 1.82 g (61.5%) of the pure compound and 0.82 g (27.7%) of the product containing traces of the starting material have been obtained.

Workup

  1. dissolutioncompletely dissolved)
  2. customis purged 3× with argon
  3. dissolutioncomplete dissolution
  4. temperatureThe reaction mixture is cooled down
  5. additiontreated with 100 mL water and 150 mL dichloromethane
  6. stirringAfter vigorous stirring at rt for one hour the organic phase
  7. customis separated
  8. washwashed twice with water (100 mL each)
  9. dry with materialdried (Na2SO4)
  10. customAfter removal of the solvent the crude product
  11. customis purified via chromatography (Isolute, dichloromethane/methanol)
  12. addition1.82 g (61.5%) of the pure compound and 0.82 g (27.7%) of the product containing traces of the starting material
  13. customhave been obtained

Sources & evidence

ORD record
ord-36d880edd1434811953e49dd9f0c6f69
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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