Trifluoroacetic acid → {2-cyano-4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acid

HRID 522291Notes

Reaction equation

HRID 522291 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[N:11]=[C:12]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH3:35])=[C:29]([C:36]([F:39])([F:38])[F:37])[CH:28]=2)[C:13]2[CH:18]=[CH:17][N:16]([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[C:14]=2[N:15]=1)#[N:9]>C(Cl)Cl>[C:8]([C:10]1[N:11]=[C:12]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH3:35])=[C:29]([C:36]([F:39])([F:38])[F:37])[CH:28]=2)[C:13]2[CH:18]=[CH:17][N:16]([CH2:19][C:20]([OH:22])=[O:21])[C:14]=2[N:15]=1)#[N:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735526tert-butyl {2-cyano-4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetate

Product 1

HCID 90065599{2-cyano-4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.41 mL) was added to a solution of tert-butyl {2-cyano-4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetate (160 mg) in CH2Cl2 (1.6 mL) at room temperature, and the mixture was stirred at the same temperature for 5 hours. After the reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (CHCl3:MeOH=100:0 to 80:20), whereby {2-cyano-4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acid (137 mg) was obtained as a white solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (CHCl3:MeOH=100:0 to 80:20)

Sources & evidence

ORD record
ord-5134f2089f994bf1a1f3c856b24971cf
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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