Water → HCID 18186469, compound

HRID 1357546Notes

Reaction equation

HRID 1357546 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:10]([C:17]1[C:22](I)=[CH:21][N:20]=[C:19]([Cl:24])[N:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C(O)C.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>[NH:10]([C:17]1[C:22]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:21][N:20]=[C:19]([Cl:24])[N:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid2×HCID 18186468HCID 18186468, compound

Product 1

HCID 18186469HCID 18186469, compoundYield 49.7%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Phenylboronic acid (240 mg, 2 mmol) and tetrakis(triphenylphosphine)palladium(0) (30 mg) were added to a solution of 4-anilino-2-chloro-5-iodopyrimidine (Method 59, 331 mg, 1 mmol) in toluene (10 ml) and ethanol (2.5 ml). 2M aqueous sodium carbonate solution (10 ml) was added and the mixture was stirred and heated under reflux for 3 hours. Further portions of phenylboronic acid (240 mg, 2 mmol) and tetrakis(triphenylphosphine) palladium(0) (30 mg) were added and the mixture was stirred and heated under reflux for 20 hours. The mixture was poured into water (100 ml) and extracted with ethyl acetate (2×50 ml). The combined extracts were washed with water (2×50 ml) and saturated sodium chloride (50 ml) and dried. Volatile material was removed by evaporation and the residue was purified by bond elute chromatography, eluting with 10-25% ethyl acetate in isohexane, to give the product (140 mg). NMR (CDCl3): 6.85 (s, 1H), 7.1 (t, 1H), 7.3 (t, 2H), 7.4 (m, 2H), 7.5-7.6 (m, 6H), 8.05 (s, 1H); MS (MH+): 282, 284.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. stirringthe mixture was stirred
  4. temperatureheated
  5. temperatureunder reflux for 20 hours
  6. extractionextracted with ethyl acetate (2×50 ml)
  7. washThe combined extracts were washed with water (2×50 ml) and saturated sodium chloride (50 ml)
  8. customdried
  9. customVolatile material was removed by evaporation
  10. customthe residue was purified by bond
  11. washelute chromatography
  12. washeluting with 10-25% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-dd68c7e09a834fe596f9732c205b7d4c
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

Loading…