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

HRID 452634ノート

反応式

HRID 452634 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ca1f1365a70f48d5bf55eb74b1c11b37
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

反応ノート

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