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

HRID 1361635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361635
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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

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 whit 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.

Aufarbeitung

  1. customThe reaction was sealed
  2. temperatureheated to 70 deg. C
  3. customovernight
  4. customresulting in the formation of whit 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

Quellen und Nachweise

ORD-Eintrag
ord-7b1d5e84315a4d4e8a4162381ace0a0c
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880000B2

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