Water → HCID 86343533, compound

HRID 516980Notes

Reaction equation

HRID 516980 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 vessel was heated at this temperature for 3.5 h. The reaction vial was removed from heat and analyzed by HPLC which showed that 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 vial 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, and the mixture 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 (ES) m/e 250 (M+H).

Workup

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

Sources & evidence

ORD record
ord-13410508804c466bb2e8312bf7aeac96
Source dataset
uspto-grants-2015_08
Patent number
US09115089B2

Reaction notes

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