Dimethylformamide → HCID 22599852, compound

HRID 1759924Notes

Reaction equation

CN(C)C=O.Cl[C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]#[C:16][CH3:17])[N:10]=[CH:9][N:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25]>C(OCC)(=O)C>[CH2:14]([O:13][C:11]1[CH:12]=[C:7]([N:26]([CH2:27][CH3:28])[CH2:24][CH3:25])[N:8]=[CH:9][N:10]=1)[C:15]#[C:16][CH3:17]

Participants

Conditions

Temperature: 50 °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 73 mg of diethylamine, followed by stirring at a bath temperature of 50° C. for 4 hours. Then, 73 mg of diethylamine was further added, followed by stirring at a bath temperature of 50° C. for 5.5 hours. Then, 146 mg of diethylamine was further added, followed by stirring at a bath temperature of 40° C. for 6 hours. The reaction mixture was left for cooling to room temperature, diluted with ethyl acetate, and washed three times with an aqueous sodium chloride solution. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel thin layer chromatography to give 136 mg of 4-(2-butynyloxy)-6-(N,N-diethylamino)pyrimidine (the present compound (144)).

Workup

stirringby stirring at a bath temperature of 50° C. for 5.5 hours
stirringby stirring at a bath temperature of 40° C. for 6 hours
waitThe reaction mixture was left
temperaturefor cooling to room temperature
washwashed three times with an aqueous sodium chloride solution
dry with materialThe organic layers were dried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-65be353800544a50886cb75d578e231b
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838463B2

Reaction notes

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