N-Methylaniline → HCID 9839798, compound

HRID 2308176Notes

Reaction equation

HRID 2308176 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 2,4dichloro-6-methyl-5-nitropyrimidine (208 mg, 1.0 mmol, 1.0 eq. in 2 mL each of EtOH and THF) is added of pyrrolidine (78mg, 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-0e22c6c33bae4e95a97dd57cb0b26447
Source dataset
uspto-grants-2004_12
Patent number
US06835726B2

Reaction notes

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