Methyl iodide → HCID 66955656, compound

HRID 1399767Notes

Reaction equation

HRID 1399767 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[O:11]=[C:12]1[NH:17][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:15][C:14]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)=[C:13]1[CH:31]([CH2:36][CH2:37][CH3:38])[C:32]([O:34][CH3:35])=[O:33].[CH3:39]I.[Cl-].[NH4+]>CN(C=O)C>[CH3:39][N:17]1[C:12](=[O:11])[C:13]([CH:31]([CH2:36][CH2:37][CH3:38])[C:32]([O:34][CH3:35])=[O:33])=[C:14]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)[N:15]=[C:16]1[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 136346168HCID 136346168, compound

Product 1

HCID 66955656HCID 66955656, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

LHMDS (1M in THF; 2 eq) is added to a cold (−10° C.) stirred solution of methyl 2-(6-oxo-2-(piperidin-1-yl)-4-p-tolyl-1,6-dihydropyrimidin-5-yl)pentanoate (1 eq) in dry DMF (2 mL/mmol of the limiting reagent). After stirring for 5 minutes, methyl iodide (2 eq) is added and the reaction mixture is stirred at room temperature for 18 hours. A saturated solution of ammonium chloride is then added and the aqueous layer is extracted with ethyl acetate. The organic layer is dried over magnesium sulphate, filtered and evaporated to dryness. The crude material is purified by flash chromatography on silica gel to provide the methyl 2-(1-methyl-6-oxo-2-(piperidin-1-yl)-4-p-tolyl-1,6-dihydropyrimidin-5-yl)pentanoate which is deprotected following general method D yielding to the title compound.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 18 hours
  2. extractionthe aqueous layer is extracted with ethyl acetate
  3. dry with materialThe organic layer is dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude material is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-37f969d2eef84be5a9728c9c48f8c987
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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