Potassium tert-butoxide → HCID 56956279, compound

HRID 2278438Notes

Reaction equation

HRID 2278438 reaction equation
CN(C)[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH: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:14]=[CH:15][N:16]=[CH:17][CH:18]=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 67513835HCID 67513835, compound

Product 1

HCID 56956279HCID 56956279, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-(dimethylamino)-1-(2-methyl-3-furanyl)-2-(4-pyridinyl)-2-propen-1-one (256 mg, 1 mmol) and 3-methyl-1-piperidinecarboximidamide hydrochloride (267 mg, 1.500 mmol) in ethanol (5 ml) was stirred at room temperature. Potassium tert-butoxide (224 mg, 2.000 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 25-50% ethyl acetate and isohexane to give 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(4-pyridinyl)pyrimidine (195 mg, 58%). A solution of 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(4-pyridinyl)pyrimidine (167 mg, 0.5 mmol) in dichloromethane (1 ml) was treated with hydrogen chloride (1M in diethyl ether, 0.6 ml). The solvent was evaporated and the residue co-evaporated with diethyl ether (×2). The residue was triturated with diethyl ether and the resulting solid was collected, washed with diethyl ether and dried to give the title compound as a yellow solid (121 mg, 65%). LC/MS [M+H]+=335. 1H NMR (400 MHz, d6-DMSO): δ 8.76 (1H, d), 8.57 (1H, s), 7.80 (2H, d), 7.51 (1H, d), 6.00 (1H, d), 4.67-4.60 (2H, m), 3.06-2.99 (1H, m), 2.67-2.76 (1H, m), 2.37 (3H, s), 1.91-1.19 (5H, m), 0.93 (3H, d).

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 25-50% ethyl acetate and isohexane

Sources & evidence

ORD record
ord-f2608a9ab83047cab76e052443c78a27
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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