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

HRID 2245223Notes

Reaction equation

HRID 2245223 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
140 °C

Procedure

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).

Workup

  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.

Sources & evidence

ORD record
ord-93561c729c284735bcad2c693e0a3499
Source dataset
uspto-grants-2010_03
Patent number
US07683058B2

Reaction notes

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