Dimethylformamide → 7H-Pyrrolo[2,3-d]pyrimidine-4-carbonitrile

HRID 452634Notes

Reaction equation

HRID 452634 reaction equation
C([N:4]1[C:8]2[N:9]=[CH:10][N:11]=[C:12](I)[C:7]=2[CH:6]=[CH:5]1)(=O)C.[CH3:14][N:15](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.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>[N:9]1[C:8]2[NH:4][CH:5]=[CH:6][C:7]=2[C:12]([C:14]#[N:15])=[N:11][CH:10]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 866400307-acetyl-4-iodo-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 552884807H-Pyrrolo[2,3-d]pyrimidine-4-carbonitrileYield 80%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-acetyl-4-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.28 g, 4.46 mmol), zinc cyanide (427 mg, 2.45 mmol), tetrakis(triphenylphosphine)palladium(0) (258 mg, 0.223 mmol) and N,N-dimethylformamide (10 mL) was tightly sealed in a vial, and the microwave was irradiated at 150° C. for 20 min. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1) to give the title compound (520 mg, yield 80%) as pale-yellow crystals.

Workup

  1. customwas tightly sealed in a vial, and the microwave
  2. customwas irradiated at 150° C. for 20 min
  3. temperatureAfter cooling
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1)

Sources & evidence

ORD record
ord-ca1f1365a70f48d5bf55eb74b1c11b37
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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