N-Methylaniline → HCID 9839798, compound

HRID 1859484Notes

Reaction equation

HRID 1859484 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.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCO.ClCCl>[CH3:18][N:19]([C:2]1[N:7]=[C:6]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7515N-MethylanilineHCID 31268PyrrolidineHCID 2752942,4-Dichloro-6-methyl-5-nitropyrimidine

Product 1

HCID 9839798HCID 9839798, 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) is added of pyrrolidine (78 mg, 1.1 eq) in 1.0 mL of EtOH. The resulting solution is stirred for 1 hour at −78° C., then for 2 hours at 0° C. N-methylaniline (0.432 mL, 4.0 eq.) is added dropwise and the reaction is stirred overnight. The resulting mixture is diluted with dichloromethane, washed with 0.1N HCl, saturated NaCl, dried (MgSO4), and filtered. Solvent is removed by evaporation and the residue is purified by chromatography to provide the target compound (r).

Workup

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

Sources & evidence

ORD record
ord-f971ade33cda4f1d994b40bd4e4c4e0e
Source dataset
uspto-grants-2003_03
Patent number
US06528513B2

Reaction notes

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