Dimethylformamide → 4-(2-Butynyloxy)-6-piperidinopyrimidine

HRID 14525

Reaction equation

HRID 14525 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+].[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C(OCC)(=O)C>[CH2:14]([O:13][C:11]1[CH:12]=[C:7]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[N:8]=[CH:9][N:10]=1)[C:15]#[C:16][CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 593411164-(2-Butynyloxy)-6-piperidinopyrimidineYield 77.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 85 mg of piperidine was added therein, and the mixture was stirred for 5 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 178 mg of 4-(2-butynyloxy)-6-piperidinopyrimidine (hereinafter, referred to as Compound (16)).

Workup

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

Sources & evidence

ORD record
ord-f5009c6f621b42c18ff9760b3dfadcbd
Source dataset
uspto-grants-2010_06
Patent number
US07732448B2

Linked notes

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