Potassium tert-butoxide → HCID 56971343, compound

HRID 2278448Notes

Reaction equation

HRID 2278448 reaction equation
CN(C)[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:5]([C:7]1[CH:11]=[CH:10][O:9][C:8]=1[CH3:12])=O.Cl.[CH3:21][CH:22]1[CH2:27][CH2:26][CH2:25][N:24]([C:28](=[NH:30])[NH2:29])[CH2:23]1.CC(C)([O-])C.[K+]>C(O)C.O>[CH3:12][C:8]1[O:9][CH:10]=[CH:11][C:7]=1[C:5]1[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:3][N:29]=[C:28]([N:24]2[CH2:25][CH2:26][CH2:27][CH:22]([CH3:21])[CH2:23]2)[N:30]=1

Participants

6

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 46736522HCID 46736522, compoundHCID 67514434HCID 67514434, compound

Product 1

HCID 56971343HCID 56971343, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-(dimethylamino)-1-(2-methyl-3-furanyl)-2-(2-pyridinyl)-2-propen-1-one (256 mg, 1 mmol) and 3-methyl-1-piperidinecarboximidamide hydrochloride (267 mg, 1.5 mmol) in ethanol (5 ml) was stirred at room temperature. Potassium tert-butoxide (224 mg, 2 mmol) was added and the mixture was heated at reflux for 45 minutes. After cooling to room temperature the reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were combined, washed with water and brine, dried and evaporated. The residue was purified by silica gel chromatography eluting with 25% ethyl acetate and isohexane followed by mass-directed automated HPLC to give 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(2-pyridinyl)pyrimidine (223 mg, 67%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 45 minutes
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. extractionextracted with ethyl acetate
  5. washwashed with water and brine
  6. customdried
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 25% ethyl acetate and isohexane

Sources & evidence

ORD record
ord-6c5b0f2109994f82ba26a8e275ff90be
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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