Hydrochloric Acid → 1-(3-Ethyl-[1,2,4]oxadiazol-5-ylmethyl)-6-phenyl-3-piperidin-4-yl-1H-thieno[3,2-d]pyrimidine-2,4-dione

HRID 1476616Notes

Reaction equation

HRID 1476616 reaction equation
[CH2:1]([C:3]1[N:7]=[C:6]([CH2:8][N:9]2[C:14]3[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[S:17][C:13]=3[C:12](=[O:24])[N:11]([CH:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)[C:10]2=[O:38])[O:5][N:4]=1)[CH3:2].Cl.O.[OH-].[Na+]>C(Cl)Cl.O1CCOCC1>[CH2:1]([C:3]1[N:7]=[C:6]([CH2:8][N:9]2[C:14]3[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[S:17][C:13]=3[C:12](=[O:24])[N:11]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:10]2=[O:38])[O:5][N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67258295HCID 67258295, compound2×

Product 1

HCID 672584241-(3-Ethyl-[1,2,4]oxadiazol-5-ylmethyl)-6-phenyl-3-piperidin-4-yl-1H-thieno[3,2-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 4-{1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate (2.79 g; compound B7) in DCM (20 ml) is reacted with a solution of hydrogen chloride in 1,4-dioxane (15 ml, 4.0 M) for 12 h at RT. Subsequently water is added (50 ml) and the pH is adjusted to about pH14 by addition of aqueous sodium hydroxide solution (5 M). The mixture is extracted with DCM (3×100 ml) and the combined organic layers are dried over sodium sulfate. After filtration and evaporation of the solvent a residue is obtained which is recrystallized from DCM to yield the title compound as a solid.

Workup

  1. extractionThe mixture is extracted with DCM (3×100 ml)
  2. dry with materialthe combined organic layers are dried over sodium sulfate
  3. filtrationAfter filtration and evaporation of the solvent a residue
  4. customis obtained which
  5. customis recrystallized from DCM

Sources & evidence

ORD record
ord-31928c351d624f159c1113d072156a02
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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