Potassium Carbonate → 4-(2-Butynyloxy)-6-(2,3-methylenedioxyphenoxy)pyrimidine

HRID 1592132Notes

Reaction equation

HRID 1592132 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]#[C:11][CH3:12])[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]1[O:27][C:26]2[C:21](=[C:22]([OH:28])[CH:23]=[CH:24][CH:25]=2)[O:20]1>CN(C)C=O>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]([O:28][C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[O:27][CH2:19][O:20][C:21]=23)[N:3]=[CH:4][N:5]=1)[C:10]#[C:11][CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5867271,3-Benzodioxol-4-olHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 225997834-(2-Butynyloxy)-6-(2,3-methylenedioxyphenoxy)pyrimidineYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 2 ml of N,N-dimethylformamide were added 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of potassium carbonate, and 138 mg of 2,3-methylenedioxyphenol, followed by stirring at 80° C. for 7 hours and then at 120° C. for 3 hours. The reaction mixture was then left for cooling to room temperature and subjected to phase separation three times between ethyl acetate and an aqueous sodium chloride solution. The organic layers were dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 193 mg of 4-(2-butynyloxy)-6-(2,3-methylenedioxyphenoxy)pyrimidine (the present compound (64)).

Workup

  1. waitat 120° C. for 3 hours
  2. waitThe reaction mixture was then left
  3. temperaturefor cooling to room temperature
  4. customsubjected to phase separation three times between ethyl acetate
  5. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d9043641d3c4abab1c5a4f6c85b844f
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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