Hydrochloric Acid → 6-(1,3-benzodioxol-5-yl)-1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride

HRID 1476639Notes

Reaction equation

HRID 1476639 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[S:18][C:17]4[C:16](=[O:19])[N:15]([CH:20]5[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]5)[C:14](=[O:33])[N:13]([CH2:34][C:35]5[N:36]=[N:37][N:38]([CH2:40][CH3:41])[N:39]=5)[C:12]=4[CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[ClH:42]>O1CCOCC1>[ClH:42].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[S:18][C:17]4[C:16](=[O:19])[N:15]([CH:20]5[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]5)[C:14](=[O:33])[N:13]([CH2:34][C:35]5[N:36]=[N:37][N:38]([CH2:40][CH3:41])[N:39]=5)[C:12]=4[CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67258894tert-butyl 4-[6-(1,3-benzodioxol-5-yl)-1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

Product 1

HCID 709762226-(1,3-benzodioxol-5-yl)-1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 4-[6-(1,3-benzodioxol-5-yl)-1-[(2-ethyl-2H-tetrazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate (239 mg; compound B50) in 1,4 dioxane (6 ml) is added a solution of hydrogen chloride in 1,4-dioxane (1.028 ml, 4.0 M). The reaction mixture is stirred for 3 d at RT. All volatiles are evaporated and the residue is treated with DCM and after removal of the solvent under reduced pressure the title compound is obtained as a solid.

Workup

  1. customAll volatiles are evaporated
  2. additionthe residue is treated with DCM
  3. customafter removal of the solvent under reduced pressure the title compound
  4. customis obtained as a solid

Sources & evidence

ORD record
ord-2ad8cd73d73d4fecbe156e8ee0216e2f
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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