Potassium tert-butoxide → HCID 56971109, compound

HRID 2278442Notes

Reaction equation

HRID 2278442 reaction equation
CN(C)[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=1)[C:5]([C:7]1[CH:11]=[CH:10][O:9][C:8]=1[CH3:12])=O.Cl.[CH3:22][CH:23]1[CH2:28][CH2:27][CH2:26][N:25]([C:29](=[NH:31])[NH2:30])[CH2:24]1.CC(C)([O-])C.[K+]>C(O)C>[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][N:16]=[C:15]([CH3:19])[CH:14]=2)=[CH:3][N:30]=[C:29]([N:25]2[CH2:26][CH2:27][CH2:28][CH:23]([CH3:22])[CH2:24]2)[N:31]=1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 46736522HCID 46736522, compoundHCID 67513546HCID 67513546, compound

Product 1

HCID 56971109HCID 56971109, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(dimethylamino)-1-(2-methyl-3-f uranyl)-2-(2-methyl-4-pyridinyl)-2-propen-1-one (541 mg, 2.000 mmol) and 3-methyl-1-piperidinecarboximidamide hydrochloride (533 mg, 3 mmol) in ethanol (10 ml) was stirred at room temperature. Potassium tert-butoxide (449 mg, 4.00 mmol) was added and the mixture was heated at reflux for 90 minutes. After cooling to room temperature the solvent was evaporated and the residue 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 in isohexane to give 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(2-methyl-4-pyridinyl)pyrimidine as a gum (460 mg, 66%). A solution of 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(2-methyl-4-pyridinyl)pyrimidine (460 mg, 1.3 mmol) in dichloromethane (2 ml) was treated with hydrogen chloride (1M in diethyl ether, 1.5 ml). The solvent was evaporated and the residue was 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 pale yellow solid (450 mg, 89%). LC/MS [M+H]+=349. 1H NMR (400 MHz, d6-DMSO): δ 8.59 (1H, d), 8.54 (1H, s), 7.81 (1H, s), 7.57-7.52 (1H, m), 7.51 (1H, d), 6.02 (1H, d), 4.70-4.60 (2H, m), 3.06-2.98 (1H, m), 2.70-2.77 (1H, m), 2.66 (3H, s), 2.39 (3H, s), 1.84-1.19 (5H, m), 0.93 (3H, d).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 90 minutes
  3. temperatureAfter cooling to room temperature the solvent
  4. customwas evaporated
  5. additionthe residue was diluted with water
  6. extractionextracted with ethyl acetate
  7. washwashed with water and brine
  8. customdried
  9. customevaporated
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with 25% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-b397adf6ec3646dba855fa13510a300a
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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