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

HRID 452634노트

반응식

HRID 452634 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ca1f1365a70f48d5bf55eb74b1c11b37
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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