Tetrahydrofuran → 2-Methyl-1-[2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-butan-1-one

HRID 1884348Notes

Reaction equation

HRID 1884348 reaction equation
[CH:1]([Mg]Cl)([CH2:3][CH3:4])[CH3:2].[CH3:7][C:8]1[N:9]=[C:10]([C:28]#N)[C:11]2[C:16]([CH3:17])=[C:15]([CH3:18])[N:14]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[C:12]=2[N:13]=1.[O:30]1CCCC1>>[CH3:2][CH:1]([CH2:3][CH3:4])[C:28]([C:10]1[C:11]2[C:16]([CH3:17])=[C:15]([CH3:18])[N:14]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[C:12]=2[N:13]=[C:8]([CH3:7])[N:9]=1)=[O:30]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 235057422,5,6-Trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine-4-carbonitrileHCID 178418314HCID 178418314, compound

Product 1

HCID 235057582-Methyl-1-[2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-butan-1-oneYield 90%

Procedure

To a solution of sec-butyl magnesium chloride (1.5 ml, 3.0 mmol, 2 M in diethyl ether) in 24 ml of dry tetrahydrofuran was added 2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine-4-carbonitrile (0.814 g, 2.67 mmol) at room temperature and stirred for 5 hours. The mixture was quenched with 5 ml of 2N HCl, neutralized with saturated sodium bicarbonate, extracted with ethyl acetate. The organic layer was dried and concentrated to give a yellow solid. The solid was purified through silica gel column chromatography using chloroform as eluent to give 0.884 g (90%) of the title compound as yellow crystals, mp 133-135° C.

Workup

  1. customThe mixture was quenched with 5 ml of 2N HCl
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give a yellow solid
  6. customThe solid was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-23115ad01e8a44d989750af6ffefde71
Source dataset
uspto-grants-2004_07
Patent number
US06765008B1

Reaction notes

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