Dimethylamine → HCID 20085265, compound

HRID 1044659Notes

Reaction equation

HRID 1044659 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([CH3:12])[N:3]=1.[CH3:13][NH:14][CH3:15]>C(OCC)(=O)C>[Cl:11][C:6]1[N:5]=[C:4]([CH3:12])[N:3]=[C:2]([N:14]([CH3:15])[CH3:13])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 831924,6-Dichloro-2-methyl-5-nitropyrimidine

Product 1

HCID 20085265HCID 20085265, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The synthesis method shall be explained concretely, and in order, below. To a solution of 4,6-dichloro-2-methyl-5-nitropyrimidine (2.65 g, 12.5 mmol) in ethyl acetate (200 ml), a 50% aqueous dimethylamine solution (1.10 ml) was dripped in at −15 degrees Celsius, this was further agitated for 1 hour, then agitated for 1 hour at 0 degrees Celsius, then at room temperature for 16 hours. The reaction liquid was poured into ice water and extraction was carried out 2 times with ethyl acetate. After washing together with the ethyl acetate layer with saturated saline, drying was done with MgSO4, and the solvent was distilled away under reduced pressure. Purification was done by silica gel chromatography (hexane:ethyl acetate=1:1), and 827.4 mg of 6-chlor-4-dimethylamino 2-methyl-5-nitropyrimidine (yield 31%) was obtained. The MS measurement result, and the NMR data for the obtained 6-chlor-4-dimethylamino-2-methyl-5-nitropyrimidine are shown below.

Workup

  1. customThe synthesis method
  2. customwas dripped in at −15 degrees Celsius
  3. stirringagitated for 1 hour at 0 degrees Celsius
  4. waitat room temperature for 16 hours
  5. customThe reaction liquid
  6. washAfter washing together with the ethyl acetate layer with saturated saline
  7. customdrying
  8. distillationthe solvent was distilled away under reduced pressure
  9. customPurification

Sources & evidence

ORD record
ord-65c6fdefb2724a6f986da576d9e75aad
Source dataset
uspto-grants-2013_10
Patent number
US08563715B2

Reaction notes

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