Trifluoroacetic acid → N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-8-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 1930722Notes

Reaction equation

HRID 1930722 reaction equation
F[C:2](F)(F)[C:3](O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([NH:22][C:23]2[N:24]=[C:25](CCC3CCCO3)[C:26]3[CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29][C:27]=3[N:28]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([NH:22][C:23]2[N:24]=[CH:25][C:26]3[CH2:32][NH:31][CH2:30][CH:29]([C:3]4[CH:2]=[CH:14][CH:15]=[CH:10][CH:11]=4)[C:27]=3[N:28]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59333773tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Product 1

HCID 44194158N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-8-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amineYield 193.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.238 mL, 3.09 mmol) was added dropwise to a stirred solution of tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.330 g, 0.62 mmol) in DCM (3 mL) at rt. The reaction mixture was stirred under reflux for 1 hr. Five equivalents of trifluoroacetic acid were added and the reaction mixture was stirred at reflux for 1 hour. The reaction mixture was allowed to cool to room temperature. The organic mixture was washed with potassium carbonate (aq) and the organic layer was separated, dried (MgSO4) and concentrated giving 0.247 g (92%) of N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-8-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine.

Workup

  1. temperatureunder reflux for 1 hr
  2. stirringthe reaction mixture was stirred
  3. temperatureat reflux for 1 hour
  4. washThe organic mixture was washed with potassium carbonate (aq)
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fe41c8ea60c342fcb7961436d26f6da9
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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