Hydrochloric Acid → Trimethylpyrimidine-5-carboxylic acid

HRID 1373462Notes

Reaction equation

HRID 1373462 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11]C)=[O:10])=[C:4]([CH3:13])[N:3]=1.CO.[OH-].[Na+].Cl>O>[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([OH:11])=[O:10])=[C:4]([CH3:13])[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 14798Sodium HydroxideHCID 137939152,4,6-Trimethyl-pyrimidine-5-carboxylic acid methyl ester

Product 1

HCID 13203797Trimethylpyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 2,4,6-trimethylpyrimidine-5-carboxylate (27 g), methanol (27 ml) and water (27 ml) were charged. 25% sodium hydroxide solution (25 ml) was charged and the batch warmed to 50° C. for 90 minutes. The batch was cooled to between −5 and 0° C. and concentrated hydrochloric acid was charged slowly, keeping the temperature within the range of −5 to +5° C. until a pH of 1.5 was reached (22.5 ml conc. HCl used). The batch was agitated for-about 1.5 hours at about 2.7° C. The solid product was recovered by filtration. The batch was dried under vacuum at 40–45° C. The 2,4,6-trimethylpyrimidine-5-carboxylic acid was recrystallized from ethyl acetate. m. p. 163–164° C., 1H NMR (CD3OD): δ2.43 (6H, s, CH3), δ2.52 (3H, s, CH3). 13H CMR (CD3OD): δ170.42, δ168.30, δ166.09, δ126.63, δ25.64, δ22.97. HR-MS; Calculated for C8H11N2O2, m/z=167.0821. Found 167.0816.

Workup

  1. temperatureThe batch was cooled to between −5 and 0° C.
  2. customwithin the range of −5 to +5° C.
  3. filtrationThe solid product was recovered by filtration
  4. customThe batch was dried under vacuum at 40–45° C
  5. customThe 2,4,6-trimethylpyrimidine-5-carboxylic acid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-01c7f526366a432e9fb8d89f8ecf9edb
Source dataset
uspto-grants-2007_01
Patent number
US07161024B2

Reaction notes

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