Acetic Acid → HCID 178433163, compound

HRID 268205Notes

Reaction equation

HRID 268205 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[C:5]([CH3:10])[N:4]=1.[C:12](O)(=O)C.[H][H].C=O>[Pd].O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH3:1][N:2]([CH3:11])[C:3]1[N:4]=[C:5]([CH3:10])[C:6]([CH3:12])=[C:7]([OH:9])[N:8]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 178418361HCID 178418361, compound3×HCID 178429399HCID 178429399, compound

Product 1

HCID 178433163HCID 178433163, compound

Reagents, catalysts & solvents 3

HCID 11192Zinc AcetateCatalystHCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Conditions

Temperature
103 °C

Procedure

38.25 Parts of 2-dimethylamino-4-hydroxy-6-methyl pyrimidine, 5 parts of zinc acetate and 7 parts of a 50% aqueous paste of 3% palladium on carbon catalyst are stirred in 180 parts of acetic acid and 180 parts of water in a closed container. Hydrogen is then passed into the reactor to a pressure of 1.5 bar. The temperature is raised to 103° C and the hydrogen pressure to 2.3 bar and 50 parts by volume of an 18% solution of formaldehyde in water are added at a uniform rate over 5 hours to the reaction mixture at 103°-110° C under 2 - 2.3 bar hydrogen pressure. After 11/2 hours the reaction mixture is cooled and the palladium on carbon catalyst removed by filtration. The filtrates are distilled under reduced pressure to remove water and acetic acid. The residue is dissolved in 325 parts of 3% aqueous sodium hydroxide, filtered, neutralised with hydrochloric acid and extracted three times with 150 parts of chloroform. The chloroform solution is evaporated to dryness to yield 33 parts of pure 2-dimethylamino-4,5-dimethyl-6-hydroxy pyrimidine.

Workup

  1. temperatureAfter 11/2 hours the reaction mixture is cooled
  2. customthe palladium on carbon catalyst removed by filtration
  3. distillationThe filtrates are distilled under reduced pressure
  4. customto remove water and acetic acid
  5. dissolutionThe residue is dissolved in 325 parts of 3% aqueous sodium hydroxide
  6. filtrationfiltered
  7. extractionextracted three times with 150 parts of chloroform
  8. customThe chloroform solution is evaporated to dryness

Sources & evidence

ORD record
ord-effe417b80ac47008afbad9fa453fded
Source dataset
uspto-grants-1976_03
Patent number
US03947440

Reaction notes

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