Hydrochloric Acid → HCID 131735712, compound

HRID 2200750Notes

Reaction equation

HRID 2200750 reaction equation
C([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C)[C:13](=[O:29])[N:12]([CH3:30])[C:11]=2[N:10]=[C:9]1[O:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[C:34]([C:39]([F:42])([F:41])[F:40])[CH:33]=1)C1C=CC=CC=1.C(Cl)Cl.Cl>C(O)C.O.C(OCC)C>[F:38][C:35]1[CH:36]=[CH:37][C:32]([O:31][C:9]2[NH:8][C:16]3[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:13](=[O:29])[N:12]([CH3:30])[C:11]=3[N:10]=2)=[CH:33][C:34]=1[C:39]([F:40])([F:42])[F:41]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 90402707HCID 90402707, compound

Product 1

HCID 131735712HCID 131735712, compoundYield 126.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Step 2 7-Benzyl-1-(3-((tert-butyldimethylsilyl)oxy)propyl)-8-(4-fluoro-3-(trifluoromethyl)phenoxy)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.44 g, 0.686 mmol) was dissolved in ethanol (15 mL) and DCM (1 mL) then 6 N aqueous HCl (2.0 mL) were added. The clear solution was stirred at room temperature. After 1 h reaction was diluted with water (100 mL) and extracted with DCM (3×75 ml). The combined extracts were dried with magnesium sulfate, filtered and the solvent was removed under reduced pressure to yield a white solid. Solid was slurried in diethyl ether (6 mL) and filtered to give 7-benzyl)-8-(4-fluoro-3-(trifluoromethyl)phenoxy)-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.35 g, 79% yield) as a white solid. LCMS retention time=3.641 min and 99% purity, LCMS MH+=493. 1H NMR (CDCl3) δ 7.23-7.52 (m, 8H), 5.47 (s, 2H), 4.20 (t, 2H, J=8 Hz), 3.47-3.54 (m, 2H), 3.43 (s, 3H), 1.88-1.92 (m, 2H).

Workup

  1. customAfter 1 h reaction
  2. extractionextracted with DCM (3×75 ml)
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customto yield a white solid
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d4a660bfc1e2491a8eeb09edd34a37c3
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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