Dimethylformamide → 4-(2-Butynyloxy)-6-(4-methylpiperidino) pyrimidine

HRID 2076854Notes

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+].[CH3:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C(OCC)(=O)C>[CH2:14]([O:13][C:11]1[CH:12]=[C:7]([N:28]2[CH2:29][CH2:30][CH:25]([CH3:24])[CH2:26][CH2:27]2)[N:8]=[CH:9][N:10]=1)[C:15]#[C:16][CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

Into 2 ml of N,N-dimethylformamide was resolved 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of potassium carbonate and 99 mg of 4-methylpiperidine was added therein, and the mixture was stirred for 4 hours at 80° C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 206 mg of 4-(2-butynyloxy)-6-(4-methylpiperidino) pyrimidine (hereinafter, referred to as Compound (18)).

Workup

additionwas added
temperatureThe reaction mixture was cooled to near room temperature
washthe mixture was washed with a saturated sodium chloride aqueous solution three times
dry with materialThe organic layers were dried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-50c73e5c97c5414cbe8d66a5e1f514a5
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928110B2

Reaction notes

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