Hydrochloric Acid → 1-(2-(2-hydroxyethoxy)ethyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione

HRID 2200545Notes

Reaction equation

HRID 2200545 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)[N:7](COCC[Si](C)(C)C)[C:6]=2[C:5](=[O:31])[N:4]([CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37]C2CCCCO2)[C:3]1=[O:44].Cl>C(O)C>[OH:37][CH2:36][CH2:35][O:34][CH2:33][CH2:32][N:4]1[C:5](=[O:31])[C:6]2[NH:7][C:8]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:21])([F:22])[F:20])[CH:13]=3)=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:44]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 904028203-methyl-1-(2-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)ethyl)-8-(3-(trifluoromethoxy)phenoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 904029761-(2-(2-hydroxyethoxy)ethyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dioneYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-methyl-1-(2-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)ethyl)-8-(3-(trifluoromethoxy)phenoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (0.64 g, 1.16 mmol,) in ethanol (15 mL) was added HCl (3 mL); then it was refluxed overnight. The solvent was concentrated to give a crude product which was purified by a column chromatography to give 1-(2-(2-hydroxyethoxy)ethyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (420 mg, 84% yield) as a white solid. LCMS retention time 1.209 min, LCMS MH+ 431.

Workup

  1. temperaturethen it was refluxed overnight
  2. concentrationThe solvent was concentrated
  3. customto give a crude product which
  4. customwas purified by a column chromatography

Sources & evidence

ORD record
ord-9f9341428f484743b7d8d322f44e9df2
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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