Trifluoroacetic acid → HCID 178450370, compound

HRID 2038160Notes

Reaction equation

HRID 2038160 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:21][CH3:22])[N:12]2C2CCCCO2)=[C:8]([NH2:23])[N:7]=1)[CH2:2][CH2:3][CH3:4].[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>CO>[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:21][CH3:22])[NH:12]2)=[C:8]([NH2:23])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 231585192-Butoxy-8-methoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine2×

Product 1

HCID 178450370HCID 178450370, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(butoxy)-8-(methoxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (for example, as prepared for Intermediate 5) (7.34 g) in methanol (100 mL) was added trifluoroacetic acid (10 mL). The mixture was stirred at ambient temperature over the weekend to give a suspension. The reaction mixture was concentrated to a small volume (thick slurry) before being diluted with ethyl acetate (50 mL). The resultant slurry was filtered and washed with a small volume of ethyl acetate until the filtrate was colourless. The solid remaining was dried by air and then in vacuo to give the title compound as a white solid (6.20 g). The filtrate obtained previously was concentrated to give a slurry which was diluted with a small volume of ethyl acetate (10 mL) and then filtered and dried as above. This second crop was isolated as a white solid (0.276 g). Both crops were identical by NMR.

Workup

  1. customto give a suspension
  2. concentrationThe reaction mixture was concentrated to a small volume (thick slurry)
  3. additionbefore being diluted with ethyl acetate (50 mL)
  4. filtrationThe resultant slurry was filtered
  5. washwashed with a small volume of ethyl acetate until the filtrate
  6. customThe solid remaining was dried by air

Sources & evidence

ORD record
ord-0804c794d251413f8c3f0884d679732d
Source dataset
uspto-grants-2013_11
Patent number
US08575340B2

Reaction notes

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