N-Methylaniline → HCID 9797328, compound

HRID 1859485Notes

Reaction equation

HRID 1859485 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[N:15]=[CH:16][NH:17][CH:18]=1.[CH3:19][NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCOCC1>[CH3:19][N:20]([C:2]1[N:7]=[C:6]([N:17]2[CH:18]=[C:14]([CH3:13])[N:15]=[CH:16]2)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 2752942,4-Dichloro-6-methyl-5-nitropyrimidineHCID 178418800HCID 178418800, compound

Product 1

HCID 9797328HCID 9797328, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,4-dichloro-6-methyl-5-nitropyrimidine (150 mg, 0.72 mmol) in dioxane (5 mL) at 80° C. was added 4-methylimidazole (60 mg, 0.72 mmol) and N-methylaniline (77 mg, 0.72 mmol). The solution was stirred overnight at 80° C., cooled, and directly chromatographed (1/1 hexane diethyl ether) to yield the title compound (t).

Workup

  1. temperaturecooled
  2. customdirectly chromatographed (1/1 hexane diethyl ether)

Sources & evidence

ORD record
ord-1fab5083be4e44a0ab7630e0190ad633
Source dataset
uspto-grants-2003_03
Patent number
US06528513B2

Reaction notes

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