Diethylamine → HCID 9882464, compound

HRID 1859483Notes

Reaction equation

HRID 1859483 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1.[CH3:13][C:14]1[NH:15][CH:16]=[CH:17][N:18]=1.[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20]>CCO.ClCCl>[CH2:19]([N:21]([C:2]1[N:7]=[C:6]([N:15]2[CH:16]=[CH:17][N:18]=[C:14]2[CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1)[CH2:22][CH3:23])[CH3:20]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 127492-MethylimidazoleHCID 2752942,4-Dichloro-6-methyl-5-nitropyrimidine

Product 1

HCID 9882464HCID 9882464, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) solution of 2,4-dichloro-6-methyl-5-nitropyrimidine (208 mg, 1.0 mmol, 1.0 eq. in 2 mL each of EtOH and THF) was added 2-methylimidazole (164 mg, 2.0 mmol, 2.0 eq.) in 2 mL of EtOH. The resulting mixture was stirred for 1 hour at −78° C., then for 2 hours at 0° C. Diethylamine (0.413 mL, 4.0 eq.) was added dropwise and the reaction was stirred overnight. The resulting mixture was diluted with dichloromethane, washed with 0.1N HCl, saturated NaCl, dried (MgSO4), and filtered. Solvent was removed by evaporation and the residue was purified by silica gel chromatography to provide 35 mg of the target compound k as an oil.

Workup

  1. waitfor 2 hours at 0° C
  2. stirringthe reaction was stirred overnight
  3. washwashed with 0.1N HCl, saturated NaCl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customSolvent was removed by evaporation
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-dc37240a8e574400bf9f0514ee1762fc
Source dataset
uspto-grants-2003_03
Patent number
US06528513B2

Reaction notes

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