Trifluoroacetic acid → HCID 90402760, compound

HRID 2200646Notes

Reaction equation

HRID 2200646 reaction equation
[Cl:1][C:2]1[CH:40]=[CH:39][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[C:12](=[O:25])[N:11]([CH3:26])[C:10]=3[N:9]=[C:8]2[O:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([F:38])([F:37])[F:36])[CH:29]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][C:18]([OH:20])=[O:19])[C:12](=[O:25])[N:11]([CH3:26])[C:10]=3[N:9]=[C:8]2[O:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([F:38])([F:36])[F:37])[CH:29]=2)=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90402960HCID 90402960, compound

Product 1

HCID 90402760HCID 90402760, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-8-(3-(trifluoromethoxy)phenoxy)-2,3,6,7-tetrahydro-1H-purin-1-yl)acetate (200 mg, 0.342 mmol) in DCM (5 ml) was added trifluoroacetic acid (2 ml, 26.9 mmol) at 0° C. The mixture was stirred at 0° C. to room temperature for 3 h. Then the mixture was concentrated, diluted with DCM and water. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give 2-(7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-8-(3-(trifluoromethoxy)phenoxy)-2,3,6,7-tetrahydro-1H-purin-1-yl)acetic acid (180 mg, 99.9% yield) as white solid. 1H-NMR (DMSO-d6) δ 13.06(s, 1H), 7.64-7.59(t, 1H), 7.55(s, 1H), 7.48-7.43(m, 5H), 7.36-7.34(d, 1H), 5.43(s, 2H), 4.53(s, 2H), 3.37(s, 3H). LCMS retention time 2.994 min; LCMS MH+ 525.

Workup

  1. concentrationThen the mixture was concentrated
  2. additiondiluted with DCM and water
  3. customThe phases were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5f7b812ae13b472b8a87968ec68c9a33
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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