Hydrochloric Acid → HCID 67518353, compound

HRID 2278443Notes

Reaction equation

HRID 2278443 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]=[C:15]([CH3:19])[CH:14]=2)=[CH:11][N:10]=[C:9]([N:20]2[CH2:25][CH2:24][CH2:23][CH:22]([CH3:26])[CH2:21]2)[N:8]=1.[ClH:27]>ClCCl>[ClH:27].[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]=[C:15]([CH3:19])[CH:14]=2)=[CH:11][N:10]=[C:9]([N:20]2[CH2:25][CH2:24][CH2:23][CH:22]([CH3:26])[CH2:21]2)[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56971109HCID 56971109, compound

Product 1

HCID 67518353HCID 67518353, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. 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-306c2c445f194567825da054e9dad1ea
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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