Sodium Bicarbonate → HCID 90402729, compound

HRID 2200666Notes

Reaction equation

HRID 2200666 reaction equation
[Cl:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][O:19]C4CCCCO4)[C:12](=[O:26])[N:11]([CH3:27])[C:10]=3[N:9]=[C:8]2[O:28][CH2:29][CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]([F:42])([F:41])[F:40])[CH:33]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CO.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][CH2:18][OH:19])[C:12](=[O:26])[N:11]([CH3:27])[C:10]=3[N:9]=[C:8]2[O:28][CH2:29][CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]([F:42])([F:40])[F:41])[CH:33]=2)=[CH:43][CH:44]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 90402874HCID 90402874, compound

Product 1

HCID 90402729HCID 90402729, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-(4-chlorobenzyl)-3-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-8-(2-(3-(trifluoromethoxy)phenoxy)ethoxy)-1H-purine-2,6(3H,7H)-dione (70 mg, 0.107 mmol) in methanol (3 mL) was added concentrated HCl (4 drops). The mixture was stirred for 1 h at room temperature. The mixture was neutralized with saturated sodium bicarbonate, and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated to give a crude product which was recrystallized from ethanol to give 7-(4-chlorobenzyl)-1-(2-hydroxyethyl)-3-methyl-8-(2-(3-(trifluoromethoxy)phenoxy)ethoxy)-1H-purine-2,6(3H,7H)-dione (16 mg, 25.6% yield) as white solid. 1H-NMR (DMSO-d6) δ 7.45-7.41(t, 1H), 7.32-7.27(m, 4H), 7.03-6.95(m, 3H), 5.19(s, 2H), 4.81(s, 2H), 4.49-4.46(t, 1H), 4.41-4.40(d, 2H), 3.91-3.88(t, 2H), 3.44-3.40(m, 5H), 1.69-1.65(t, 2H). LCMS retention time 3.142 min; LCMS MH+ 569.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product which
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-7b1894be885941a89f9ff1fb7a454844
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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