Potassium Carbonate → 4-(2-butynyloxy)-6-(N-ethyl-N-isopropylamino)pyrimidine

HRID 1759893Notes

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

Participants

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-ethylisopropylamine, followed by stirring at 60° C. for 7 hours. Then, 166 mg of potassium carbonate and 435 mg of N-ethylisopropylamine were added, and the mixture was stirred at 80° C. for 8 hours. Then, 166 mg of potassium carbonate and 435 mg of N-ethylisopropylamine were added, and the mixture was stirred at 120° C. for 5 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 preparative silica gel thin layer chromatography to give 79 mg of 4-(2-butynyloxy)-6-(N-ethyl-N-isopropylamino)pyrimidine (the present compound (105)).

Workup

stirringthe mixture was stirred at 80° C. for 8 hours
stirringthe mixture was stirred at 120° C. for 5 hours
waitThe reaction mixture was then left
temperaturefor cooling to room temperature
customsubjected to phase separation three times between ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-80ef352169594f269aa788c1e7a9db3d
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838463B2

Reaction notes

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