Trifluoroacetic acid → HCID 178448285, compound

HRID 2036340Notes

Reaction equation

HRID 2036340 reaction equation
[CH3:1][C@H:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([O:22][CH3:23])[N:13]2C2CCCCO2)=[C:9]([NH2:24])[N:8]=1)[CH2:3][CH2:4][CH3:5].[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>CO>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[CH3:1][C@H:2]([O:6][C:7]1[NH:8][C:9]([NH2:24])=[C:10]2[C:14]([N:15]=1)=[N:13][C:12]([O:22][CH3:23])=[N:11]2)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 576996248-methoxy-2-(((S)-pentan-2-yl)oxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 178448285HCID 178448285, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (6 g, 17.89 mmol) was dissolved in methanol (50 ml). Trifluoroacetic acid (20.67 ml, 268 mmol) was added dropwise, and the mixture stirred at 20° C. for 72 hours under an atmosphere of nitrogen. The solvent was removed in vacuo, and the resulting solid was washed with ethyl acetate and filtered. The filtrate was stripped and the residue washed with ethyl acetate. The combined solid residues were dried in the vacuum oven for 2 hours to give the title compound as an off-white solid (5.3 g).

Workup

  1. customThe solvent was removed in vacuo
  2. washthe resulting solid was washed with ethyl acetate
  3. filtrationfiltered
  4. washthe residue washed with ethyl acetate
  5. customThe combined solid residues were dried in the vacuum oven for 2 hours

Sources & evidence

ORD record
ord-cced86093a0b4fd097fdd9875eb9e0f0
Source dataset
uspto-grants-2013_11
Patent number
US08575181B2

Reaction notes

Loading…