Potassium Carbonate → HCID 22599807, compound

HRID 1592170Notes

Reaction equation

HRID 1592170 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]([NH:21][CH2:22][CH2:23][CH3:24])[CH3:20]>CN(C)C=O>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]([N:21]([CH2:19][CH3:20])[CH2:22][CH2:23][CH3:24])[N:3]=[CH:4][N:5]=1)[C:10]#[C:11][CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 883981-Propanamine, N-ethyl-2×HCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 22599807HCID 22599807, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °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 87 mg of N-ethylpropylamine, followed by stirring at 60° C. for 7 hours. Then, 166 mg of potassium carbonate and 87 mg of N-ethylpropylamine were added, and the mixture was stirred at a bath temperature of 60° C. for 6 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 layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel thin layer chromatography to give 136 mg of 4-(2-butynyloxy)-6-(N-ethyl-N-propylamino)pyrimidine (the present compound (104)).

Workup

  1. stirringthe mixture was stirred at a bath temperature of 60° C. for 6 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 layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-916d20902f024a3ea0abb245b156cfa4
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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