Potassium Carbonate → 4-Methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carbonitrile

HRID 1876758Notes

Reaction equation

HRID 1876758 reaction equation
[C:1]([C:4](=[CH:7]N(C)C)[C:5]#[N:6])(=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:17][N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26][NH:27][C:28]([NH2:30])=[NH:29])[CH2:20][CH2:19]1>C(O)C>[CH3:2][C:1]1[C:4]([C:5]#[N:6])=[CH:7][N:30]=[C:28]([NH:27][CH2:26][CH2:25][CH2:24][CH:21]2[CH2:20][CH2:19][N:18]([CH3:17])[CH2:23][CH2:22]2)[N:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59154395HCID 59154395, compoundHCID 178480300HCID 178480300, compound

Product 1

HCID 445457774-Methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 5-L round-bottom flask equipped with overhead mechanical stirrer, nitrogen inlet, and thermocouple probe were added 2-acetyl-3-dimethylamino-acrylonitrile (103.65 g, 0.75 mol), anhydrous potassium carbonate (powdered, not granular) (165.85 g, 1.2 mol), and N-[3-(1-methyl-piperidin-4-yl)-propyl]-guanidine (119.02 g, 0.60 mol) in ethanol (2.125 L). The resultant mixture was heated to reflux with stirring and held for 24 h. The resultant mixture was then concentration and the resultant residue partitioned between ethyl acetate (1.5 L) and 1 N NaOH (1.5 L). The layers were separated and the aqueous layer was extracted with additional ethyl acetate (2×1.5 L). The combined organic layers were concentrated to yield the title compound as a solid.

Workup

  1. customTo a 5-L round-bottom flask equipped with overhead mechanical stirrer, nitrogen inlet
  2. temperatureto reflux
  3. concentrationconcentration
  4. customthe resultant residue partitioned between ethyl acetate (1.5 L) and 1 N NaOH (1.5 L)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with additional ethyl acetate (2×1.5 L)
  7. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-2ccd96ddfe854127b51f6dc7d3451caf
Source dataset
uspto-grants-2012_11
Patent number
US08309720B2

Reaction notes

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