Cesium carbonate → HCID 18336822, compound

HRID 2297685Notes

Reaction equation

HRID 2297685 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:23][C@H:22]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]2[O:13][C:14](=[O:16])[CH3:15])=[C:4](Cl)[N:3]=1.[Cl:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[C:33]([F:38])[CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:19]([O:18][C@H:17]1[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([Cl:1])=[N:3][C:4]=3[NH:35][C:34]2[CH:36]=[CH:37][C:31]([Cl:30])=[CH:32][C:33]=2[F:38])[O:23][C@@H:22]1[CH2:24][O:25][C:26](=[O:28])[CH3:27])(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 938984-Chloro-2-fluoroanilineHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine

Product 1

HCID 18336822HCID 18336822, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 2,6-dichloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine 2(1.09) in toluene (25 ml) was added palladium acetate (50 mg), 4-chloro-2-fluoroaniline (0.5 ml) and bis[2-(diphenylphosphino)phenyl] ether 3(120 mg) and the reaction stirred at 20° C. for 15 min. Caesium carbonate (872 mg) was added and the mixture heated at 90° C. for 16 hours. The reaction mixture was cooled to 20° C. and partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was washed with brine (100 ml), dried with magnesium sulphate and the solvent removed in vacuo. Purification by flash chromatography on silica gel, eluting with ethyl acetate:cyclohexane (1:1) gave the title compound (400 mg).

Workup

  1. temperaturethe mixture heated at 90° C. for 16 hours
  2. temperatureThe reaction mixture was cooled to 20° C.
  3. custompartitioned between ethyl acetate (100 ml) and water (100 ml)
  4. washThe organic layer was washed with brine (100 ml)
  5. dry with materialdried with magnesium sulphate
  6. customthe solvent removed in vacuo
  7. customPurification by flash chromatography on silica gel
  8. washeluting with ethyl acetate:cyclohexane (1:1)

Sources & evidence

ORD record
ord-197b21d2365b497d9c2b670bdaf11bb9
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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