Sulfuric Acid → HCID 59843349, compound

HRID 552311Notes

Reaction equation

HRID 552311 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3[N:14]=[C:15]([CH3:28])[N:16]=[C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][C:26]#[N:27])[CH2:20][CH2:19]4)[C:12]=3[C:11]([CH3:29])=[C:10]2[CH3:30])=[C:4]([CH3:31])[CH:3]=1.[OH:32]S(O)(=O)=O.[OH-].[Na+]>>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3[N:14]=[C:15]([CH3:28])[N:16]=[C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][C:26]([NH2:27])=[O:32])[CH2:20][CH2:19]4)[C:12]=3[C:11]([CH3:29])=[C:10]2[CH3:30])=[C:4]([CH3:31])[CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67152512HCID 67152512, compound

Product 1

HCID 59843349HCID 59843349, compound

Procedure

To 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-propionitrile (0.40 g), H2SO4 (4 mL) was added and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into ice, and then was made to alkaline by adding 4 M aqueous NaOH solution. The mixture was extracted with ethyl acetate and the organic phase and the organic phase was dried over Na2SO4. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified with column chromatography (silica gel: Wako gel C200, eluent: CHCl3:methanol=60/1) to obtain an oil. The oily product was crystallized from diethylether to obtain the title compound (0.33 g) as a white crystal.

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organic phase and the organic phase was dried over Na2SO4
  4. customThe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: CHCl3:methanol=60/1)
  7. customto obtain an oil
  8. customThe oily product was crystallized from diethylether

Sources & evidence

ORD record
ord-e3d2275bd32d4e1d9cf4321aecd542e2
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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