Hydrochloric Acid → HCID 86702428, compound

HRID 2278439Notes

Reaction equation

HRID 2278439 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:11][N:10]=[C:9]([N:19]2[CH2:24][CH2:23][CH2:22][CH:21]([CH3:25])[CH2:20]2)[N:8]=1.[ClH:26]>ClCCl>[ClH:26].[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7]1[C:12]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:11][N:10]=[C:9]([N:19]2[CH2:24][CH2:23][CH2:22][CH:21]([CH3:25])[CH2:20]2)[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56956279HCID 56956279, compound

Product 1

HCID 86702428HCID 86702428, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. customThe solvent was evaporated
  2. customThe residue was triturated with diethyl ether
  3. customthe resulting solid was collected
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-37bda22731044e549d2607f796b73f23
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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