Acetone → HCID 18706828, compound

HRID 1421874Notes

Reaction equation

HRID 1421874 reaction equation
[NH2:1]O.[NH2:3][C:4]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6](Cl)[N:5]=1.[CH2:12]([OH:14])[CH3:13].C(N([CH2:20][CH3:21])CC)C.[CH3:22][C:23]([CH3:25])=O>>[NH2:3][C:4]1[N:5]=[C:6]([NH:1][CH:13]([CH2:12][OH:14])[CH:21]2[CH2:20][CH2:25][CH:23]=[CH:22]2)[CH:7]=[C:8]([Cl:10])[N:9]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 702EthanolHCID 787HydroxylamineHCID 8471TriethylamineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 18706828HCID 18706828, compoundYield 33.8%

Procedure

To the amino alcohol compound D (1.27 g, 0.01 mol) were added 2-amino-4,6-dichloropyrimidine (1.64 g, 0.01 mol), ethanol (40 ml) and triethylamine (2.1 ml), and the mixture was refluxed for one day. The solvent was distilled away under reduced pressure. Ethyl acetate was added to the residue and the mixture was subjected to hot filtration. The solvent of the filtrate was distilled away under reduced pressure and the residue was isolated by silica gel column chromatography (chloroform:methanol=50:1) to give colorless prism crystals (0.86 g, 33.8%) of the objective compound (compound No. 50), m.p. 201-203° C. (acetone).

Workup

  1. temperaturethe mixture was refluxed for one day
  2. distillationThe solvent was distilled away under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. filtrationthe mixture was subjected to hot filtration
  5. distillationThe solvent of the filtrate was distilled away under reduced pressure
  6. customthe residue was isolated by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-5238cc2410fa4610b4ca370fb6e326fd
Source dataset
uspto-grants-2000_06
Patent number
US06080750

Reaction notes

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