Diisopropylethylamine → N-methyl-4-(2-(4-nitrophenoxy)phenyl)pyrimidin-2-amine

HRID 446287Notes

Reaction equation

HRID 446287 reaction equation
Cl.CN.CS([C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[CH:11]=[CH:10][N:9]=1)(=O)=O.C[CH2:31][N:32](C(C)C)C(C)C>CC(O)C>[CH3:31][NH:32][C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 669703952-(Methylsulfonyl)-4-(2-(4-nitrophenoxy)phenyl)pyrimidine

Product 1

HCID 66970416N-methyl-4-(2-(4-nitrophenoxy)phenyl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of methylamine hydrochloride (0.863 g, 12.8 mmol), 2-(methylsulfonyl)-4-(2-(4-nitrophenoxy)phenyl)pyrimidine (0.791 g, 2.13 mmol) in iPrOH was added n,n-diisopropylethylamine (2.60 ml, 14.9 mmol). The reaction was sealed and heated to 70 deg. C. overnight. The resulting clear yellow solution was judged complete by LCMS in the morning. The reaction was cooled to ambient temperature, resulting in the formation of white crystals. Filter, rinsing with isopropanol. Concentrate filtrate, partition between EtOAc and 1N NaOH. Dry over anhyd. Na2SO4, filter, concentrate to give N-methyl-4-(2-(4-nitrophenoxy)phenyl)pyrimidin-2-amine as a light yellow solid. MS m/z=323 [M+1]+. Calc'd for C17H14N4O3: 322.32.

Workup

  1. customThe reaction was sealed
  2. temperatureheated to 70 deg. C
  3. customovernight
  4. customresulting in the formation of white crystals
  5. filtrationFilter
  6. washrinsing with isopropanol
  7. customConcentrate filtrate, partition between EtOAc and 1N NaOH
  8. customDry over anhyd
  9. filtrationNa2SO4, filter
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-e0db69fc28e64cff9167fcedaeff023b
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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