Hydrochloric Acid → 7-benzyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione

HRID 2200684Notes

Reaction equation

HRID 2200684 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][O:21]C3CCCCO3)[C:13](=[O:28])[N:12](COCC[Si](C)(C)C)[C:11]=2[N:10]=[C:9]1[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([O:44][C:45]([F:48])([F:47])[F:46])[CH:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:13](=[O:28])[NH:12][C:11]=2[N:10]=[C:9]1[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([O:44][C:45]([F:46])([F:48])[F:47])[CH:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 904027997-benzyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-8-(3-(trifluoromethoxy)phenoxy)-3-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 904026367-benzyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dioneYield 123%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 7-benzyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-8-(3-(trifluoromethoxy)phenoxy)-3-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (5.3 g, 7.68 mmol) in ethyl alcohol (20 mL) was added concentrated HCl (5 mL). The reaction was stirred at 80° C. overnight. The reaction was concentrated and the residue was neutralized with saturated sodium bicarbonate. This aqueous phase was extracted with ethyl acetate and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give 7-benzyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (4.5 g, 100% yield) as white solid. 1H-NMR (DMSO-d6) δ 11.93(s, 1H), 7.62-7.57(t, 1H), 7.44-7.32(m, 8H), 5.42(s, 2H), 4.49-4.46(t, 1H), 3.89-3.86(t, 2H), 3.46-3.41(m, 2H), 1.72-1.65(m, 2H). LCMS retention time 2.560 min; LCMS MH+ 477.

Workup

  1. concentrationThe reaction was concentrated
  2. extractionThis aqueous phase was extracted with ethyl acetate
  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-ffaf4511cae94449847b19e38dff4138
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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