Acetonitrile → Ethyl 3-methyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]butanoate

HRID 1962686Notes

Reaction equation

HRID 1962686 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1.[C:23]([OH:28])(=[O:27])[CH:24]=[CH:25][CH3:26].[CH2:29]1CCN2C(=NCCC2)C[CH2:30]1.[C:40](#N)C>>[CH3:26][C:25]([N:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1)([CH3:40])[CH2:24][C:23]([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 194992-Butenoic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 426313464-(1H-Pyrazol-4-yl)-7-(2-(trimethylsilyl)ethoxy)methyl-7 H-pyrrolo(2,3-d)-pyrimidine

Product 1

HCID 66597630Ethyl 3-methyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]butanoateYield 910%

Procedure

A solution of 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (12.1 g, 0.0384 mol), 2-butenoic acid, 3-methyl-, ethyl ester (16.0 mL, 0.115 mol) and DBU (14.3 mL, 0.0959 mol) in ACN (100 mL) was heated at reflux for 3.5 hours. The solvent was removed in vacuo. The residue was diluted with water, extracted with ethyl acetate, and the combined organic extracts were washed with saturated ammonium chloride, dried over sodium sulfate, and concentrated. The crude residue was purified by flash column chromatography (ethyl acetate/hexanes) to yield the desired product (15.5 g, 910%).

Workup

  1. temperatureat reflux for 3.5 hours
  2. customThe solvent was removed in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washthe combined organic extracts were washed with saturated ammonium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4defcc98017e4e87a042fd9c03d3cd5c
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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