Trifluoroacetic acid → Ammonium Hydroxide

HRID 2243669Notes

Reaction equation

HRID 2243669 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:36][CH:37]3[CH2:42][CH2:41][N:40](C(OC(C)(C)C)=O)[CH2:39][CH2:38]3)[N:17]=[C:18]([C:19]3[CH:24]=[C:23]([C:25]([NH:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH:22]=[CH:21][C:20]=3[CH3:35])[C:13]=2[CH2:12][NH:11][C:10]1=[O:50].FC(F)(F)C(O)=O>C(Cl)Cl>[NH4+:9].[OH-:26].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:36][CH:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)[N:17]=[C:18]([C:19]3[CH:24]=[C:23]([CH:22]=[CH:21][C:20]=3[CH3:35])[C:25]([NH:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:26])[C:13]=2[CH2:12][NH:11][C:10]1=[O:50]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11952412HCID 11952412, compound

Product 2

HCID 14923Ammonium HydroxideHCID 11952411HCID 11952411, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The compound 1,1-dimethylethyl 4-{[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}-1-piperidinecarboxylate, (0.052 g, 0.0076 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 1 M NaOH. The organic phase was washed with H2O (2×), brine (1×), dried over anhydrous Na2SO4, filtered and evaporated. The residue was flash chromatographed on silica gel (10 g) eluted with 6:2:0.2, CH2Cl2:ethanol:NH4OH to give the title compound as a white amorphous solid. mp (dec) 172-176° C.; LC-MS m/z 584 (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 1 M NaOH
  4. washThe organic phase was washed with H2O (2×), brine (1×)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customchromatographed on silica gel (10 g)
  9. washeluted with 6:2:0.2, CH2Cl2

Sources & evidence

ORD record
ord-7a9c93fb63c043d1a515099aa7d960ca
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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