Trifluoroacetic acid → 5-methyl-7-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-5H-pyrrolo[3,2-d]pyrimidine

HRID 532483Notes

Reaction equation

HRID 532483 reaction equation
[CH3:1][N:2]1[C:10]2[C:9]([O:11][CH:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)=[N:8][CH:7]=[N:6][C:5]=2[C:4]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:3]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][N:2]1[C:10]2[C:9]([O:11][CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[N:8][CH:7]=[N:6][C:5]=2[C:4]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57414748tert-butyl 4-(5-methyl-7-(4-methanesulfonyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 574147495-methyl-7-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-5H-pyrrolo[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-(5-methyl-7-(4-methanesulfonyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)piperidine-1-carboxylate obtained in Example 25, dichloromethane (1 mL) and trifluoroacetic acid (1 mL) were added, and stirred for 1 hour. After completion of the reaction, the reaction was terminated with saturated sodium bicarbonate, and dichloromethane layer was extracted and washed with a saline solution. Subsequently, the washed layer was dried over anhydrous sodium sulfate, and filtered and distilled under reduced pressure to obtain the title compound.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction was terminated with saturated sodium bicarbonate, and dichloromethane layer
  3. extractionwas extracted
  4. washwashed with a saline solution
  5. dry with materialSubsequently, the washed layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-826f73f89d584be98273971b1148cdbc
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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