Sodium Carbonate → HCID 15949464, compound

HRID 2220480Notes

Reaction equation

HRID 2220480 reaction equation
[NH2:1][C:2]1[N:3]([CH3:23])[C:4](=[O:22])[C:5]([C:14]2[CH:15]=[C:16]([C:20]#[N:21])[N:17]([CH3:19])[CH:18]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9](Br)[CH:8]=2)[N:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[N:30]1[CH:35]=[C:34](B(O)O)[CH:33]=[N:32][CH:31]=1.CO.C(Cl)(Cl)Cl>CCOCC.CCCCCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:3]([CH3:23])[C:4](=[O:22])[C:5]([C:14]2[CH:15]=[C:16]([C:20]#[N:21])[N:17]([CH3:19])[CH:18]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:34]3[CH:35]=[N:30][CH:31]=[N:32][CH:33]=3)[CH:8]=2)[N:6]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 15949461HCID 15949461, compoundHCID 21584188Chloroform methanol

Product 1

HCID 15949464HCID 15949464, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21584099Diethylether hexaneSolvent

Conditions

Temperature
100 °C

Procedure

The toluene/ethanol (1/1) solvent mixture was deoxygenated vigorously with nitrogen gas prior to using in this reaction. A mixture of 4-[2-amino-4-(3-bromophenyl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile (173 mg, 0.465 mmol), sodium carbonate (148 mg, 1.394 mmol), pyrimidine-5-boronic acid (86.4 mg, 0.697 mmol) and tetrakis(triphenylphosphine)palladium(0) (27 mg, 0.023 mmol) in toluene/ethanol (1/1) solvent mixture (10 mL) was heated in a 100° C. oil bath for eight hours. TLC (5% methanol/chloroform) shows complete conversion to a new material. The solvent was removed by evaporation and the residue dissolved in chloroform and washed with water. The organic phase was dried (Na2SO4), filtered and evaporated. The resultant residue was purified by HPLC (Luna CN column, normal mobile phase). Crystallization from warm ethyl acetate/hexane afforded the title product as a pure crystalline material, mp 214-225° C.; MS (ES) m/z 370.1.

Workup

  1. customThe toluene/ethanol (1/1) solvent mixture was deoxygenated vigorously with nitrogen gas
  2. customto using in this reaction
  3. customThe solvent was removed by evaporation
  4. dissolutionthe residue dissolved in chloroform
  5. washwashed with water
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe resultant residue was purified by HPLC (Luna CN column, normal mobile phase)
  10. customCrystallization
  11. temperaturefrom warm ethyl acetate/hexane

Sources & evidence

ORD record
ord-4eb9d77706434232a70f3c2e29fce9a9
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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