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

HRID 1476651Notes

Reaction equation

HRID 1476651 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[N:10]=[C:9]([CH2:11][N:12]2[C:17]3[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[S:20][C:16]=3[C:15](=[O:27])[N:14]([CH:28]3[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]3)[C:13]2=[O:41])[O:8][N:7]=1.C(OCC)C.[ClH:47]>O1CCOCC1>[ClH:47].[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[N:10]=[C:9]([CH2:11][N:12]2[C:17]3[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[S:20][C:16]=3[C:15](=[O:27])[N:14]([CH:28]3[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]3)[C:13]2=[O:41])[O:8][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67258411HCID 67258411, compound

Product 1

HCID 672582531-{[3-(3-methoxypropyl)-1,2,4-oxadiazol-5-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-{[3-(3-methoxypropyl)-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 (780 mg, compound B68) is dissolved in a solution of hydrogen chloride in 1,4-dioxane (20 ml, 6.8 M). The reaction mixture is stirred for 30 min at RT. Then diethyl ether is added and the resulting precipitate is filtered off, washed with diethyl ether and dried in vacuo to afford the title compound as a solid.

Workup

  1. filtrationthe resulting precipitate is filtered off
  2. washwashed with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-5c7e7d8fa39d4205a749a930101836a3
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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