Sulfuric Acid → HCID 14281075, compound

HRID 2231646Notes

Reaction equation

HRID 2231646 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]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[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]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:23]=2)[N:16]=1

Participants

10

Reactant 6

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 69515632,2-DiethylpropanedioateHCID 14281141HCID 14281141, compound

Product 1

HCID 14281075HCID 14281075, compoundYield 86.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To tetrahydrofuran (30 ml) were added diethylmalonate (1.6 g) and 60% oily sodium hydride (0.4 g), and then 4-chloro-6-methyl-2-(6-phenyl-2-pyridinyl)pyrimidine (2 g). The mixture was heated under refluxing for 30 minutes. Sodium hydroxide (0.85 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 (1.4 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; n-hexane:acetone=3:1 in volume) to give 4,6-dimethyl-2-(6-phenyl-2-pyridinyl)pyrimidine (1.6 g, yield 86%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing for 30 minutes
  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-01006dce3f57465e90557d5acab9a50d
Source dataset
uspto-grants-1988_11
Patent number
US04783466

Reaction notes

Loading…