Tributylamine → HCID 178517377, compound

HRID 605601Notes

Reaction equation

HRID 605601 reaction equation
[CH:1]1([C:8](=O)[CH:9]([C:15]2[C:20]([F:21])=[CH:19][C:18]([F:22])=[CH:17][C:16]=2[F:23])[C:10]([O:12]CC)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:25][C:26]1[NH:27][CH:28]=[CH:29][N:30]=1.C(N(CCCC)CCCC)CCC>C(OCC)(=O)C>[CH:1]1([C:8]2[N:27]3[CH:28]=[CH:29][N:30]=[C:26]3[N:25]=[C:10]([OH:12])[C:9]=2[C:15]2[C:16]([F:23])=[CH:17][C:18]([F:22])=[CH:19][C:20]=2[F:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 821402-AminoimidazoleHCID 67047753HCID 67047753, compound

Product 1

HCID 178517377HCID 178517377, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of ethyl 3-cycloheptyl-3-oxo-2-(2,4,6-trifluorophenyl)propanoate (342 mg, 1.0 mmol), 2-aminoimidazole (Helv. Acta. Chim. 76, 2066 (1993))(83 mg, 1.0 mmol), and 0.5 mL of tributylamine is stirred under nitrogen atmosphere at 160° C. for 1.5 h and cooled to room temperature. The mixture is dissolved in ethyl acetate and the organic layer is washed with 1.0 N hydrochloric acide (×2) and saturated sodium chloride, dried over magnesium sulfate, and concentrated to give crude 5-cycloheptyl-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidin-7-ol as a dark oil (294 mg).

Workup

  1. temperaturecooled to room temperature
  2. washthe organic layer is washed with 1.0 N hydrochloric acide (×2) and saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e6126517a19c42a68ad96ac3e467e5c9
Source dataset
uspto-grants-2011_03
Patent number
US07915266B2

Reaction notes

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