Hydrochloric Acid → HCID 118023451, compound

HRID 2171815Notes

Reaction equation

HRID 2171815 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7].[H-].[Na+].CS(O[CH2:15][C:16]1[C:17]2[CH:25]=[C:24]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[S:23][C:18]=2[N:19]=[C:20]([CH3:22])[N:21]=1)(=O)=O.Cl>O.CN(C=O)C.C1COCC1>[CH:26]1([C:24]2[S:23][C:18]3[N:19]=[C:20]([CH3:22])[N:21]=[C:16]([CH2:15][N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][C:2]4=[O:7])[C:17]=3[CH:25]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 126652-PiperidoneHCID 24758Sodium hydrideHCID 118023431HCID 118023431, compound

Product 1

HCID 118023451HCID 118023451, compoundYield 8.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of piperidin-2-one (100 mg), THF (4 mL), and DMF (1 mL) was added NaH (60% oil, 40 mg), followed by stirring at room temperature for 30 minutes, and then (6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl methanesulfonate (150 mg) was added thereto, followed by further stirring at room temperature for 1 hour. To the reaction mixture were added water and 1 M hydrochloric acid, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column (hexane/EtOAc) to obtain 1-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]piperidin-2-one (13 mg).

Workup

  1. stirringby further stirring at room temperature for 1 hour
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-b2cc1a8da0114c6facf9446a69bc2282
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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