Water → HCID 86343533, compound

HRID 2199518Notes

Reaction equation

HRID 2199518 reaction equation
CC1(C)O[C:6](=[O:8])[CH:5]=[C:4]([CH2:9][C:10](=O)[CH3:11])[O:3]1.[Cl:14][C:15]1[CH:20]=[C:19]([NH2:21])[C:18]([CH3:22])=[CH:17][N:16]=1.O>O1CCOCC1>[Cl:14][C:15]1[CH:20]=[C:19]([N:21]2[C:10]([CH3:11])=[CH:9][C:4]([OH:3])=[CH:5][C:6]2=[O:8])[C:18]([CH3:22])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 126437062-Chloro-5-methylpyridin-4-amineHCID 146384202,2-dimethyl-6-(2-oxopropyl)-1,3-dioxin-4-one

Product 1

HCID 86343533HCID 86343533, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a screw top vial with rubber septa inset was added 2,2-dimethyl-6-(2-oxo-propyl)-[1,3]dioxin-4-one, prepared as described in Organic Letters, 11(21), 4910-4913; 2009, (500 mg, 2.7 mmol) and 2-chloro-5-methyl-pyridin-4-ylamine (575 mg, 4 mmol, 1.5 eq). The mixture was dissolved in anhydrous 1,4-dioxane (10 mL). Once the mixture was homogeneous the vial was placed on a stirrer/hot plate preset to 90° C. The reaction was heated at this temperature for 3.5 h. The reaction was removed from heat and analyzed by HPLC which showed the reaction was >95% complete. The vial was placed back on the hot plate. To the heated mixture was added H2SO4 (250 μL) and the reaction was heated for 1 h. The reaction was removed from the heat and after cooling to ambient temperature, the dioxane was removed by passing a stream of air over the top of the open vial to give a brown residue. Water (˜4 mL) was added to the vial, which was stirred for 30 min. The resulting tan solid was filtered off with washing from additional water and the diethyl ether to give the desired product (531 mg, 57% based on being the sulfate salt) as a tan solid which by HPLC was ˜95% pure: MS (M+H) 250.

Workup

  1. customprepared
  2. customwas placed on a stirrer/hot plate preset to 90° C
  3. temperatureThe reaction was heated at this temperature for 3.5 h
  4. customThe reaction was removed
  5. temperaturefrom heat
  6. additionTo the heated mixture was added H2SO4 (250 μL)
  7. temperaturethe reaction was heated for 1 h
  8. customThe reaction was removed from the
  9. temperatureheat
  10. customthe dioxane was removed
  11. customto give a brown residue
  12. filtrationThe resulting tan solid was filtered off
  13. washwith washing from additional water

Sources & evidence

ORD record
ord-e9ed6e4543df4529b6706b2730d53d9c
Source dataset
uspto-grants-2016_06
Patent number
US09359300B2

Reaction notes

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