HCID 57474818, compound → HCID 57474820, compound

HRID 391705Notes

Reaction equation

HRID 391705 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]=[C:15]3[C:11]([NH:12][C:13](=[O:24])[N:14]3[CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:10]([C:25]([O:27]C)=O)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Si](OC1C=C(C2N=C3C(NC(=O)N3CC3CCOCC3)=C(C(OC)=O)[N:54]=2)C=CC=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]=[C:15]3[C:11]([NH:12][C:13](=[O:24])[N:14]3[CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:10]([C:25]([NH2:54])=[O:27])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 57474818HCID 57474818, compoundHCID 57474819HCID 57474819, compound

Product 1

HCID 57474820HCID 57474820, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

Methyl 2-(3-hydroxyphenyl)-8-oxo-9-((tetrahydro-2H-pyran-4-yl)methyl)-8,9-dihydro-7H-purine-6-carboxylate. Methyl 2-(3-(tert-butyldiphenylsilyloxy)phenyl)-8-oxo-9-((tetrahydro-2H-pyran-4-yl)methyl)-8,9-dihydro-7H-purine-6-carboxylate (0.202 g, 0.367 mmol) was dissolved in tetrahyrdrofuran (10 mL) and tetrabutylammonium fluoride on silica gel (0.294 g, 0.404 mmol) was added to the solution. The solution stirred at ambient temperature for two h. LCMS confirms product and no starting materials. The solution was filtered and condensed to give the crude title compound (0.110 g, 58%).

Workup

  1. additionwas added to the solution
  2. filtrationThe solution was filtered
  3. customcondensed

Sources & evidence

ORD record
ord-a74d73b82e2e4ebfa0fcfe1f95502721
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

Loading…