Water → 4-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-N-phenylpyrimidin-2-amine

HRID 1295879

Reaction equation

HRID 1295879 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:19](=O)[C:20]#[CH:21])=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[N+]([O-])([O-])=O.[C:27]1([NH:33][C:34]([NH2:36])=[NH2+:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O.CCOCC>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:19]3[CH:20]=[CH:21][N:36]=[C:34]([NH:33][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:35]=3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 112321611-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-oneHCID 178418786HCID 178418786, compound

Product 1

HCID 102741414-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-N-phenylpyrimidin-2-amineYield 50%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-2-propyn-1-one (58 mg, 0.19 mmol) in 1-methyl-2-pyrrolidinone (2 mL) was added N-phenylguanidinium nitrate (185 mg, 0.94 mmol) and potassium carbonate (129 mg, 0.94 mmol). The mixture was heated at 140° C. for 1.25 hours and then cooled to room temperature. Water was added then ether. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 hexanes-ethyl acetate) provided 4-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-N-phenylpyrimidin-2-amine (40 mg, 50%) as a yellow solid. 1H NMR (CDCl3 with 2 drops CD3OD): δ 9.45 (d, 1 H), 8.16 (d, 1 H), 7.60–7.58 (m, 2 H), 7.39 (d, 1 H), 7.34–7.29 (m, 3 H), 7.17–7.15 (m, 2 H), 7.07 (t, 1 H), 6.95 (m, 1 H), 6.75 (t, 1 H), 6.58 (d, 1 H), 3.79 (s, 3 H); MS m/z 428 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with brine
  3. extractionThe aqueous layer was extracted with ether
  4. dry with materialthe combined organics dried over magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-0f2f6b2591e948fd9c25b5ce7a735576
Source dataset
uspto-grants-2007_07
Patent number
US07244740B2

Linked notes

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