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

HRID 2199552Notes

Reaction equation

HRID 2199552 reaction equation
C(OC(=O)[N:5]([C:16]1[N:21]=[C:20]([CH3:22])[C:19]([C:23]#[N:24])=[CH:18][N:17]=1)[CH2:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1)C.[OH-].[Na+]>CO>[CH3:22][C:20]1[C:19]([C:23]#[N:24])=[CH:18][N:17]=[C:16]([NH:5][CH2:6][CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[N:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67083915(5-Cyano-4-methyl-pyrimidin-2-yl)-[3-(1-methyl-piperidin-4-yl)-propyl]-carbamic acid ethyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100 ml 3-neck flask, (5-cyano-4-methyl-pyrimidin-2-yl)-[3-(1-methyl-piperidin-4-yl)-propyl]-carbamic acid ethyl ester (1.4 g, 4.05 mmol) was dissolved in MeOH (16.0 g). The resultant solution was cooled to about 0-5° C., and then a sodium hydroxide solution [prepared from NaOH (0.6 g) and water (1.2 g)] was added at about 0-5° C. The resultant mixture was stirred at 0° C., then warmed to ambient temperature over 3 h. The reaction was monitored by HPLC. The resultant mixture was concentrated by rotary evaporation at about 20-25° C. and the resultant solid was slurried in water (20 g), overnight at ambient temperature. The solid was collected by filtration, washed with water (20 g) and dried in a vacuum oven at about 70-80° C. overnight to yield the title compound.

Workup

  1. concentrationThe resultant mixture was concentrated by rotary evaporation at about 20-25° C.
  2. filtrationThe solid was collected by filtration
  3. washwashed with water (20 g)
  4. customdried in a vacuum oven at about 70-80° C. overnight

Sources & evidence

ORD record
ord-46a949c0f4d549f8bbae893305ac9416
Source dataset
uspto-grants-2016_06
Patent number
US09359327B2

Reaction notes

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