Diethylamine → HCID 9882464, compound

HRID 1531676Notes

Reaction equation

HRID 1531676 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-784f48b9ec2448b4a0c29cdc2771b042
Source dataset
uspto-grants-2001_03
Patent number
US06200977B1

Reaction notes

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