Trifluoroacetic acid → HCID 178448286, compound

HRID 2367963Notes

Reaction equation

HRID 2367963 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[N:15]=[C:14]2[C:10]([N:11]=[C:12]([O:22][CH3:23])[NH:13]2)=[C:9]([NH2:24])[N:8]=1)[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-amine2×

Product 1

HCID 178448286HCID 178448286, compound

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) (for example as prepared for Intermediate 6) 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-169aaac2787e495db05091ce4b66dc20
Source dataset
uspto-grants-2014_04
Patent number
US08703754B2

Reaction notes

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