Potassium Phosphate, Tribasic → HCID 9921947, compound

HRID 478238Notes

Reaction equation

HRID 478238 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[N:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].B1([C:39]2[CH:44]=[CH:43][CH:42]=[N:41][CH:40]=2)OCCCO1>O1CCOCC1.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>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:39]4[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[N:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 86759229HCID 86759229, compound

Product 1

HCID 9921947HCID 9921947, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a degassed solution of trifluoromethanesulfonic acid 3-(7-methyl-imidazo[1,2-a]pyrimidin-3-yl)phenyl ester (0.1 g, 0.28 mmol) in 1,4-dioxane (3 ml) was added potassium phosphate (0.119 g, 0.56 mmol), pyridine-3-boronic acid 1,3-propanediol cyclic ester (0.092 g, 0.56 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.016 g, 13.8 mmol) and the mixture heated at 80° C. for 22 h. After cooling to ambient temperature the solvent was evaporated in vacuo. The residue was stirred with 10% methanol in dichloromethane and the solid material filtered off. The filtrate was applied to two preparative TLC plates (silica gel) and eluted with 6% methanol in dichloromethane. The appropriate band was collected and processed to give an oil which crystallised from diethyl ether as a white solid (26 mg): δH (400 MHz, CDCl3) 2.67 (3H, s), 6.80 (1H, d, J 7), 7.42 (1H, td, J 8 and 1), 7.57 (1H, m), 7.65 (2H, m), 7.71 (1H, s), 7.86 (1H, s), 7.92 (1H, m), 8.53 (1H, d, J 7), 7.65 (1H, m), 8.89 (1H, s); m/z (ES+) 287 (M++H).

Workup

  1. temperatureAfter cooling to ambient temperature the solvent
  2. customwas evaporated in vacuo
  3. filtrationthe solid material filtered off
  4. washeluted with 6% methanol in dichloromethane
  5. customThe appropriate band was collected
  6. customto give an oil which
  7. customcrystallised from diethyl ether as a white solid (26 mg)

Sources & evidence

ORD record
ord-a896717df97244cfa758596d3043bf95
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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