Acetic Acid → HCID 178433163, compound

HRID 268203Notes

Reaction equation

HRID 268203 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, compound2×HCID 178429399HCID 178429399, compound

Product 1

HCID 178433163HCID 178433163, compound

Reagents, catalysts & solvents 3

HCID 11192Zinc AcetateCatalystHCID 23938PalladiumCatalystHCID 962WaterSolvent3×

Conditions

Temperature
100 °C

Procedure

382.5 Parts of 2-dimethylamino-4-hydroxy-6-methylpyrimidine, 50 parts of zinc acetate and 35 parts of a 50% aqueous paste of a 3% palladium on carbon catalyst are stirred in 2500 parts of acetic acid and 1000 parts of water in a closed container. Hydrogen is then passed into the reaction vessel to a pressure of 3 bar and the temperature is raised to 100° C. 285 parts of 36% formaldehyde diluted with 500 parts of water are added over 6 hours, maintaining a hydrogen pressure of 3 bar and temperature of 98°- 100° C., followed by the addition of 1075 parts of water. The reaction mixture is stirred under these conditions for a further 17 hours, and then cooled and the palladium on carbon catalyst is removed by filtration. The filtrates are distilled under reduced pressure to remove water and acetic acid and to the residue 2500 parts of water and 150 parts of 32% sodium hydroxide solution are added. The suspension is heated to 60° C. and filtered, the filter cake washed with 22 parts of 32% sodium hydroxide solution diluted with 1000 parts of water. The combined filtrates and washes are adjusted to pH 6 with 100 parts of 35% hydrochloric acid and extracted with chloroform. The chloroform is removed by distillation to yield 283 parts of 2-dimethylamino-4,5-dimethyl-6-hydroxypyrimidine, analysing at 95% strength.

Workup

  1. additionare added over 6 hours
  2. temperaturecooled
  3. customthe palladium on carbon catalyst is removed by filtration
  4. distillationThe filtrates are distilled under reduced pressure
  5. customto remove water and acetic acid
  6. additionto the residue 2500 parts of water and 150 parts of 32% sodium hydroxide solution are added
  7. temperatureThe suspension is heated to 60° C.
  8. filtrationfiltered
  9. washthe filter cake washed with 22 parts of 32% sodium hydroxide solution
  10. additiondiluted with 1000 parts of water
  11. extractionextracted with chloroform
  12. customThe chloroform is removed by distillation

Sources & evidence

ORD record
ord-471a3204731a4da3a6a3397425a834ab
Source dataset
uspto-grants-1976_03
Patent number
US03947440

Reaction notes

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