Sulfuric Acid → 4,6-Dimethyl-2-(6-n-propyl-2-pyridinyl)pyrimidine

HRID 580320Notes

Reaction equation

HRID 580320 reaction equation
[CH2:1](C(CC)(C([O-])=O)C([O-])=O)C.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][CH3:30])[N:23]=2)[N:16]=1.[OH-].[Na+].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O.CO.O1CCCC1>[CH3:1][C:15]1[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][CH3:30])[N:23]=2)[N:16]=1

Participants

10

Reactant 6

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 69515632,2-DiethylpropanedioateHCID 142532544-Chloro-6-methyl-2-(6-n-propyl-2-pyridinyl)pyrimidine

Product 1

HCID 142531944,6-Dimethyl-2-(6-n-propyl-2-pyridinyl)pyrimidineYield 70.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To tetrahydrofuran (30 ml) were added diethylmalonate (0.9 g) and 60 % oily sodium hydride (0.23 g), and then 4-chloro-6-methyl-2-(6-n-propyl-2-pyridinyl)pyrimidine (1 g). The mixture was heated under refluxing for one hour. Sodium hydroxide (0.49 g) solution in water (10 ml) and methanol (10 ml) was added thereto, and the mixture was further heated under refluxing for 20 minutes. After the mixture was left to stand until it was cooled to room temperature, sulfuric acid (0.8 g) was added dropwise thereto. The mixture was heated under refluxing for 30 minutes and left to stand to room temperature. 1-N aqueous sodium carbonate solution was added until a mixture was neutralized and concentrated under reduced pressure. The residue was subjected to silica-gel column chromatography (eluent; hexane:acetone=3:1) to give 4,6-dimethyl-2-(6-n-propyl-2-pyridinyl)pyrimidine (0.65 g) as resinous substance.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing for one hour
  3. temperaturethe mixture was further heated
  4. temperatureunder refluxing for 20 minutes
  5. waitAfter the mixture was left
  6. temperatureThe mixture was heated
  7. temperatureunder refluxing for 30 minutes
  8. waitleft
  9. customto stand to room temperature
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d9f13e2543c42b4803e53b591dae7d7
Source dataset
uspto-grants-1988_06
Patent number
US04752608

Reaction notes

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