Hydrochloric Acid → 6-Methyl-3-(2-pyrimidinyl)-2-pyridinecarboxylic acid

HRID 1094759Notes

Reaction equation

HRID 1094759 reaction equation
[CH3:1][C:2]1[N:7]=C(C#N)[C:5]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1.[OH-:16].[Na+].Cl.[CH3:19][CH2:20][OH:21]>O>[CH3:1][C:2]1[N:7]=[C:19]([C:20]([OH:16])=[O:21])[C:5]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 593637436-Methyl-3-(2-pyrimidinyl)-2-pyridinecarbonitrile

Product 1

HCID 584779466-Methyl-3-(2-pyrimidinyl)-2-pyridinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

An alternative method to make D19 is as follows: 6-methyl-3-(2-pyrimidinyl)-2-pyridinecarbonitrile D18 (0.481 g) was suspended in EtOH (5 ml) and a solution of NaOH (0.490 g, 12.26 mmol) in water (5 ml) was added. The yellow mixture was stirred at 100° C. overnight. The yellow solution was cooled to 25° C. and HCl 6 M (1.0 ml) was added dropwise till pH=4.5. The solvent was removed to give a yellow powder that was dried at 50° C./vacuum for 1.5 hours to give the title compound D19 (1.242 g).

Workup

  1. temperatureThe yellow solution was cooled to 25° C.
  2. customThe solvent was removed
  3. customto give a yellow powder that
  4. customwas dried at 50° C./vacuum for 1.5 hours

Sources & evidence

ORD record
ord-f8a8ff688e7d4a85ae073dfc8112655c
Source dataset
uspto-grants-2012_03
Patent number
US08133908B2

Reaction notes

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