Hydrogen chloride-ethyl acetate → 2-[(3S)-2-azabicyclo[2.2.2]oct-3-yl]-6-(5-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride

HRID 1052192Notes

Reaction equation

HRID 1052192 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]1[S:15][C:14]2[C:13](=[O:16])[NH:12][C:11]([C@@H:17]3[CH:22]4[CH2:23][CH2:24][CH:19]([CH2:20][CH2:21]4)[N:18]3C(OC(C)(C)C)=O)=[N:10][C:9]=2[CH:8]=1.[ClH:32].C(OCC)(=O)C>CO>[ClH:32].[ClH:32].[CH:19]12[CH2:20][CH2:21][CH:22]([CH2:23][CH2:24]1)[C@@H:17]([C:11]1[NH:12][C:13](=[O:16])[C:14]3[S:15][C:7]([C:3]4[CH:4]=[N:5][NH:6][C:2]=4[CH3:1])=[CH:8][C:9]=3[N:10]=1)[NH:18]2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 136333934tert-butyl (3S)-3-[6-(5-methyl-1H-pyrazol-4-yl)-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl]-2-azabicyclo[2.2.2]octane-2-carboxylate

Product 1

HCID 1363339352-[(3S)-2-azabicyclo[2.2.2]oct-3-yl]-6-(5-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl(3S)-3-[6-(5-methyl-1H-pyrazol-4-yl)-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl]-2-azabicyclo[2.2.2]octane-2-carboxylate (143 mg) produced in Example 106, step B, in methanol (3.0 mL) was added 4M hydrochloric acid/ethyl acetate solution (1.0 mL) with stirring at room temperature. The reaction system was stirred with heating at 50° C. for 1 hr, and the precipitate was collected by filtration, and washed with ethyl acetate to give the title compound (128 mg) as a colorless solid.

Workup

  1. stirringThe reaction system was stirred
  2. temperaturewith heating at 50° C. for 1 hr
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-3d03dcca9728474fbbb430b85f39aef8
Source dataset
uspto-grants-2016_07
Patent number
US09388195B2

Reaction notes

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