Water → HCID 66913179, compound

HRID 1044655Notes

Reaction equation

HRID 1044655 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]([N+:14]([O-:16])=[O:15])=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:3]=1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1.O>N1CCCCC1>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH:23]=[CH:1][C:2]2[N:3]=[C:4]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[N:7]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 312444-MethoxybenzaldehydeHCID 3576386HCID 3576386, compound

Product 1

HCID 66913179HCID 66913179, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

The synthesis method shall be explained concretely, and in order, below. A solution of 2-methyl-4,6-dimorpholino-5-nitropyrimidine (1.13 g, 3.65 mmol) and p-anisaldehyde (3.50 ml, 29.3 mmol) in piperidine (5 ml) was agitated under heating for 4 hours at 130 degrees Celsius. Water was added, and extraction was carried out 2 times using ethyl acetate. After washing the organic 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 535 mg of 2-[2-(4-methoxyphenyl)vinyl]-4,6-dimorpholino-5-nitropyrimidine (yield 58%) was obtained. The NMR data for the obtained 2-[2-(4-methoxyphenyl)vinyl]-4,6-dimorpholino-5-nitropyrimidine is shown below.

Workup

  1. customThe synthesis method
  2. temperatureunder heating for 4 hours at 130 degrees Celsius
  3. extractionextraction
  4. washAfter washing the organic layer with saturated saline
  5. customdrying
  6. distillationthe solvent was distilled away under reduced pressure
  7. customPurification

Sources & evidence

ORD record
ord-85b4e4a317494244858b8ce4bcae0a25
Source dataset
uspto-grants-2013_10
Patent number
US08563715B2

Reaction notes

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