Trifluoroacetic acid → 1-methyl-2-[1-(4-piperazin-1-ylmethyl-phenyl)piperidin-4-yloxy]-1H-[4,4']bipyrimidinyl-6-one

HRID 1468777Notes

Reaction equation

HRID 1468777 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:41]=[CH:40][C:25]([CH2:26][N:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[CH:24][C:25]([CH2:26][N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[CH:40][CH:41]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 50939811Tert-butyl 4-{4-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yloxy)piperidin-1-yl]benzyl}piperazine-1-carboxylate

Product 1

HCID 509398121-methyl-2-[1-(4-piperazin-1-ylmethyl-phenyl)piperidin-4-yloxy]-1H-[4,4']bipyrimidinyl-6-oneYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-{4-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yloxy)piperidin-1-yl]benzyl}piperazine-1-carboxylate (470 mg, 0.83 mmol) in dichloromethane (4.2 ml) was added trifluoroacetic acid (3.9 g, 34 mmol) at room temperature. The mixture was stirred overnight. After concentration under reduced pressure, the residue was dissolved into water. The aqueous solution was washed with ethyl acetate and basified with potassium carbonate. Extraction with chloroform was performed three times and the organic layer was dried over sodium sulfate, concentrated in vacuo to afford 1-methyl-2-[1-(4-piperazin-1-ylmethyl-phenyl)piperidin-4-yloxy]-1H-[4,4′]bipyrimidinyl-6-one as a pale yellow solid (260 mg, 0.56 mmol, 67%).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue was dissolved into water
  3. washThe aqueous solution was washed with ethyl acetate
  4. extractionExtraction with chloroform
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93b99c8b6aca4e769e4df4eacd92f4a0
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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