Potassium Carbonate → HCID 22599807, compound

HRID 1759892Notes

Reaction equation

HRID 1759892 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-eb71d13b975a476aa8f8421f91f5a701
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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