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

HRID 1476647Notes

Reaction equation

HRID 1476647 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[O:39][N:38]=[C:37]([CH2:40][CH3:41])[N:36]=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[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)[C:14](=[O:33])[N:13]([CH2:34][C:35]5[O:39][N:38]=[C:37]([CH2:40][CH3:41])[N:36]=5)[C:12]=4[CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 67258594tert-butyl 4-[6-(1,3-benzodioxol-5-yl)-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

Product 1

HCID 672591926-(1,3-benzodioxol-5-yl)-1-[(3-ethyl-1,2,4-oxadiazol-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-DioxaneSolvent3×

Procedure

To a solution of tert-butyl 4-[6-(1,3-benzodioxol-5-yl)-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate (3.75 g; compound B64) in 1,4 dioxane (130 ml) is added a solution of hydrogen chloride in 1,4-dioxane (31 ml, 4.0 M). The reaction mixture is stirred for 12 h at RT. To complete the reaction an additional amount of a solution of hydrogen chloride in 1,4-dioxane (5.0 ml, 4.0 M) is added and the mixture is stirred for 20 h at RT. Subsequently the suspension is filtered to give title compound as a solid.

Workup

  1. additionis added
  2. stirringthe mixture is stirred for 20 h at RT
  3. filtrationSubsequently the suspension is filtered

Sources & evidence

ORD record
ord-6e03f2c8fecf4324af284d7d922030c5
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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