Cesium fluoride → HCID 18186443, compound

HRID 1357548Notes

Reaction equation

HRID 1357548 reaction equation
[NH:1]([C:8]1[C:13](I)=[CH:12][N:11]=[C:10]([Cl:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:16]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17]1.[F-].[Cs+]>C1COCC1.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:1]([C:8]1[C:13]([C:18]2[CH:19]=[CH:20][O:16][CH:17]=2)=[CH:12][N:11]=[C:10]([Cl:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 2734358Furan-3-boronic acidHCID 18186468HCID 18186468, compound

Product 1

HCID 18186443HCID 18186443, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-anilino-2-chloro-5-iodopyrimidine (Method 59, 331 mg, 1 mmol), 3-furylboronic acid (224 mg, 2 mmol), caesium fluoride (400 mg, 2 mmol) and tetrakis(triphenylphosphine)palladium(0) (30 mg) in THF (10 ml) was stirred and heated at reflux for 20 hours under a nitrogen atmosphere. Insoluble material was removed by filtration and the filtrate was concentrated. The residue was purified by bond elute chromatography, eluting with 25% ethyl acetate in isohexane, to give the product (140 mg). NMR (CDCl3): 6.6 (d, 1H), 7.0 (br s, 1H), 7.15 (t, 1H), 7.25 (s, 1H), 7.4 (t, 2H), 7.55 (d, 2H), 7.65 (d, 2H), 8.1 (s, 1H); MS (MH+): 272, 274.

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 hours under a nitrogen atmosphere
  3. customInsoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by bond
  6. washelute chromatography
  7. washeluting with 25% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-ed05ffd9190a4c8092b10cde0c9dbda3
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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