Potassium Phosphate, Tribasic → 4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbaldehyde

HRID 400565Notes

Reaction equation

HRID 400565 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:14]=[O:15])[O:12][CH:13]=2)O1.Cl[C:18]1[C:19]2[CH:26]=[CH:25][NH:24][C:20]=2[N:21]=[CH:22][N:23]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C>[N:21]1[C:20]2[NH:24][CH:25]=[CH:26][C:19]=2[C:18]([C:9]2[CH:10]=[C:11]([CH:14]=[O:15])[O:12][CH:13]=2)=[N:23][CH:22]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 35475414-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehydeHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 576473994-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g [4.5 mMols] of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde, 550 mg [3.6 mMols]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine and 1.52 g [6.7 mMols] of tripotassium phosphate were placed in 20 mL DMF and 10 mL water and purged with nitrogen gas while stirring for 10 minutes at ambient temperature. To this stirring suspension, 400 mg, 0.45 mMols] of tetrakistriphenylphosphine palladium (0) was added in one portion, and reaction vessel was placed in a preheated bath at 110° C. The reaction was stirred and heated under a nitrogen atmosphere for 30 minutes (deemed complete by analytical liquid chromatography). The reaction mixture was cooled and suction filtered to remove the ligand present as a precipitate, which was washed with a little DMF/H2O 2:1. The combined filtrates were reduced in volume to one quarter of the original under reduced pressure and diluted slowly with water with stirring. The resulting fine precipitate was centrifuged down and the pellet was washed with more water, re-centrifuged and transferred to a RB with acetonitrile. This solvent was reduced to dryness under reduced pressure. The material, 670 mg (yield 87%) of a light beige powder was carried on without further purification. LC/ms m+1=214.

Workup

  1. custom10 mL water and purged with nitrogen gas
  2. additionTo this stirring suspension, 400 mg, 0.45 mMols] of tetrakistriphenylphosphine palladium (0) was added in one portion, and reaction vessel
  3. customwas placed in a preheated bath at 110° C
  4. stirringThe reaction was stirred
  5. temperatureheated under a nitrogen atmosphere for 30 minutes (deemed complete by analytical liquid chromatography)
  6. temperatureThe reaction mixture was cooled
  7. filtrationsuction filtered
  8. customto remove the ligand present as a precipitate
  9. washwhich was washed with a little DMF/H2O 2:1
  10. additiondiluted slowly with water
  11. stirringwith stirring
  12. washthe pellet was washed with more water

Sources & evidence

ORD record
ord-13274d73471f416dbcaa43c6b1a6ea00
Source dataset
uspto-grants-2014_06
Patent number
US08741912B2

Reaction notes

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