Potassium Carbonate → 5-(1,4,5,6-Tetrahydropyrimidin-1-yl)-3-methyl-2-nitro aniline

HRID 1767021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767021
F[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[NH:13]1[CH2:18][CH2:17][CH2:16][N:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[N:15]1([C:2]2[CH:3]=[C:4]([CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=2)[NH2:7])[CH2:16][CH2:17][CH2:18][N:13]=[CH:14]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 1371051,4,5,6-TetrahydropyrimidineHCID 220210255-Fluoro-3-methyl-2-nitroaniline

Produkt 1

HCID 235418765-(1,4,5,6-Tetrahydropyrimidin-1-yl)-3-methyl-2-nitro anilineAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of 2.0 g (11.76 mmol) of the 5-Flouro-3-methyl-2-nitro aniline in 10 mL of DMSO was added 1.2 g (14.11 mmol) of 1,4,5,6-Tetrahydropyrimidine, and 2.43 g (17.64 mmol) of potassium carbonate, and the mixture was heated at 100° C. for 10 hrs, cooled, diluted with water, and extracted with Ethylacetate containing 5% methanol. The combined organic extract was washed with water, brine and dried (Na2SO4). Evaporation of the solvent furnished the residue, which was chromatographed (20% of 2M ammonia in methanol and dichloromethane) to produce 1.85 g (67%) of the product as red solid. 1H NMR (400 MHz, CD3OD) δ 7.89 (1H, s), 6.53 (1H, d, J=2.57 Hz), 6.44 ((1H, d, J=2.1 Hz), 7.04 (1H, d, J=2.1 Hz), 3.70 (2H, t, J=6.0 Hz), 3.41 (2H, t, J=5.65 Hz, 2.43 (3H, s), 2.05 (2H, m) LCMS (M+H)+ m/z 235 (t=0.78 min).

Aufarbeitung

  1. temperaturecooled
  2. extractionextracted with Ethylacetate containing 5% methanol
  3. extractionThe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent
  7. customfurnished the residue, which
  8. customwas chromatographed (20% of 2M ammonia in methanol and dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-3d99b6dd5a17471e81643ebd522ce561
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07232826B2

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