Trifluoroacetic acid → Ammonium Hydroxide

HRID 2243666Notes

Reaction equation

HRID 2243666 reaction equation
CC([CH2:5][N:6]([CH2:10][CH2:11][NH:12][C:13]1[N:14]=[C:15]([C:32]2[CH:37]=[C:36]([C:38]([NH:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:39])[CH:35]=[CH:34][C:33]=2[CH3:48])[C:16]2[CH2:21][NH:20][C:19](=[O:22])[N:18]([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=3[F:30])[C:17]=2[N:31]=1)C(=O)[O-:8])(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH4+:6].[OH-:8].[F:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([F:29])[C:23]=1[N:18]1[C:17]2[N:31]=[C:13]([NH:12][CH2:11][CH2:10][NH:6][CH3:5])[N:14]=[C:15]([C:32]3[CH:37]=[C:36]([CH:35]=[CH:34][C:33]=3[CH3:48])[C:38]([NH:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:39])[C:16]=2[CH2:21][NH:20][C:19]1=[O:22]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86608556HCID 86608556, compound

Product 2

HCID 14923Ammonium HydroxideHCID 11952233HCID 11952233, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The compound 1,1-dimethylethyl(2-{[8-(2,6-difluorophenyl)-4-(2-methyl-5-{[(phenylmethyl)amino]carbonyl}phenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-2-yl]amino}ethyl)methylcarbamate, (0.036 g, 0.055 mmol) was dissolved in CH2Cl2 (4 mL) and stirred under argon at 0° C. Trifluoroacetic acid (1 mL) was added and the mixture stirred under argon at 0° C. for 2 h. The solvents were pumped off in vacuo, and the residue was partitioned between EtOAc and H2O. The mixture was made basic by the addition of 1M NaOH. The organic phase was washed with H2O (2×), with brine (1×), dried over anhydrous Na2SO4, filtered and evaporated. The residue was flash chromatographed on silica gel (10 g) eluted with 6:1:0.05, CH2Cl2:isopropanol:NH4OH to give the title compound as a white amorphous solid. mp 157-161° C.; LC-MS m/z 558 (M+H)+, 1.49 min (ret. time).

Workup

  1. stirringthe mixture stirred under argon at 0° C. for 2 h
  2. customthe residue was partitioned between EtOAc and H2O
  3. additionThe mixture was made basic by the addition of 1M NaOH
  4. washThe organic phase was washed with H2O (2×), with brine (1×)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customchromatographed on silica gel (10 g)
  9. washeluted with 6:1:0.05, CH2Cl2

Sources & evidence

ORD record
ord-46cee63ab6ae4d9eb3901148e88a9ff7
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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