Hydrochloric Acid → HCID 67513207, compound

HRID 2278441Notes

Reaction equation

HRID 2278441 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:14]=[N:15][CH: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.[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]=[N:15][CH: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 56971108HCID 56971108, compound

Product 1

HCID 67513207HCID 67513207, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(dimethylamino)-1-(2-methyl-3-furanyl)-2-(3-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 to give 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(3-pyridinyl)pyrimidine (28 mg, 8%). A solution of 4-(2-methyl-3-furanyl)-2-(3-methyl-1-piperidinyl)-5-(3-pyridinyl)pyrimidine (28 mg, 0.084 mmol) in dichloromethane (1 ml) was treated with hydrogen chloride (1M in diethyl ether, 0.1 ml). The solvent was evaporated and the residue co-evaporated with dichloromethane (×2). The resulting solid was dried to give the title compound as a solid (24 mg, 77%). LC/MS [M+H]+=335. 1H NMR (400 MHz, d6-DMSO): δ 8.75-8.73 (2H, m), 8.45 (1H, s), 8.17 (1H, d), 7.86-7.82 (1H, m), 7.45 (1H, d), 5.87 (1H, d), 4.65-4.59 (2H, m), 3.02-2.95 (1H, m), 2.71-2.65 (1H, m), 2.38 (3H, s), 1.91-1.18 (5H, m), 0.92 (3H, d).

Workup

  1. customThe solvent was evaporated
  2. customThe resulting solid was dried

Sources & evidence

ORD record
ord-25fa7ff52af94e2ab9384ebf0f235f63
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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