Potassium Carbonate → Xanthine

HRID 2200548Notes

Reaction equation

C[N:2]1[C:10]2[N:9]=[C:8](OC3C=CC=C(OC(F)(F)F)C=3)[N:7](COCC[Si](C)(C)C)[C:6]=2[C:5](=[O:31])[NH:4][C:3]1=[O:32].BrCCCOC1CCCCO1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH:4]1[C:5](=[O:31])[C:6]2[NH:7][CH:8]=[N:9][C:10]=2[NH:2][C:3]1=[O:32]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-methyl-8-(3-(trifluoromethoxy)phenoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (1.0 g, 2.12 mmol, intermediate 12, step 2) in DMF (10 mL) was added 2-(3-bromopropoxy)tetrahydro-2H-pyran (0.57 g, 2.54 mmol, intermediate 3) and potassium carbonate (0.88 g, 6.36 mmol). The reaction was heated at 50° C. for 3 h. The mixture was cooled, partitioned between ethyl acetate and water. The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether/ethyl acetate (1:3) to give 3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-8-(3-(trifluoromethoxy)phenoxy)-7-(2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (0.9 g, 70.0% yield) as a white solid. LCMS retention time 2.270 min, LCMS MH+-THP 531.

Workup

temperatureThe mixture was cooled
custompartitioned between ethyl acetate and water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give a crude product which
customwas purified by column chromatography
washeluting with petroleum ether/ethyl acetate (1:3)

Sources & evidence

ORD record: ord-19ed0f488c5f4c6eadedb0a044f432a6
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359359B2

Reaction notes

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