Hydrochloric Acid → 1-[(1-ethyl-1H-pyrazol-4-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride

HRID 1476607Notes

Reaction equation

HRID 1476607 reaction equation
[CH2:1]([N:3]1[CH: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])[CH:5]=[N:4]1)[CH3:2].[ClH:39]>O1CCOCC1>[ClH:39].[CH2:1]([N:3]1[CH: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])[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67258778tert-butyl 4-{1-[(1-ethyl-1H-pyrazol-4-yl)methyl]-2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate

Product 1

HCID 672581211-[(1-ethyl-1H-pyrazol-4-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 4-{1-[(1-ethyl-1H-pyrazol-4-yl)methyl]-2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate (763 mg; compound B18) is dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml, 4.0 M). The solution is stirred for 1 h at RT. The resulting precipitate is filtered off, washed with diethyl ether and dried to give the crude title compound. To remove impurities the free base is submitted to flash column chromatography (silica gel, eluent: MeOH). The purified free base of the title compound is taken up in diethyl ether and the solution is treated with chlorotrimethylsilane. The resulting precipitate is filtered off and dried to afford the title compound as a solid.

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with diethyl ether
  3. customdried
  4. customto give the crude title compound
  5. customTo remove impurities the free base
  6. additionthe solution is treated with chlorotrimethylsilane
  7. filtrationThe resulting precipitate is filtered off
  8. customdried

Sources & evidence

ORD record
ord-6c66a07b522a4d4e8b0b09fc8c16fdad
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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