Ethanol → 4-(4,6-Dimethylpyrimidin-2-yl)morpholine

HRID 2245223

Reaktionsgleichung

Reaktionsgleichung von HRID 2245223
Br.[O:2]1[CH2:7][CH2:6][N:5]([C:8]([NH2:10])=[NH:9])[CH2:4][CH2:3]1.C(O)C.[C:14]([CH2:17][C:18](=O)[CH3:19])(=O)[CH3:15]>>[CH3:15][C:14]1[CH:17]=[C:18]([CH3:19])[N:10]=[C:8]([N:5]2[CH2:6][CH2:7][O:2][CH2:3][CH2:4]2)[N:9]=1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 31261AcetylacetoneHCID 2806564Morpholine-4-carboximidamide Hydrobromide

Produkt 1

HCID 6768024-(4,6-Dimethylpyrimidin-2-yl)morpholineAusbeute 90 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a suspension of morpholinoformamidine hydrobromide (2.0 g, 9.52 mmol) in ethanol (6 ml) potassium tert-butoxide (1.068 g, 9.52 mmol) then acetylacetone (2 ml, 20 mmol) were added. The reaction mixture was flashed with argon, sealed in the Emrys process vial and heated under microwave irradiation at 140° C. for 5 min. After cooling it was quenched with ethyl acetate (50 ml), filtered via plug of SiO2 (5 g) and eluted with ethyl acetate. Volatiles were removed in vacuo at 70° C. to furnish 1.65 g of pale brown oil that solidified overnight. Yield 90%. LC-MS (m/z) 193.9 (MH+); tR=0.71. 1H NMR (500 MHz, DMSO-d6): 2.23 (s, 6H), 3.62 (m, 4H), 3.67 (m, 4H), 6.44 (s, 1H).

Aufarbeitung

  1. customsealed in the Emrys process vial
  2. temperatureAfter cooling it
  3. customwas quenched with ethyl acetate (50 ml)
  4. filtrationfiltered via plug of SiO2 (5 g)
  5. washeluted with ethyl acetate
  6. customVolatiles were removed in vacuo at 70° C.

Quellen und Nachweise

ORD-Eintrag
ord-93561c729c284735bcad2c693e0a3499
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683058B2

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