Tributylamine → HCID 178517381, compound

HRID 1181250Notes

Reaction equation

HRID 1181250 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH:10]([C:16]([O:18]CC)=O)[C:11]([O:13]CC)=O.[NH2:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.C(N(CCCC)CCCC)CCC>C(OCC)(=O)C>[F:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[C:3]=1[C:10]1[C:11]([OH:13])=[N:21][C:22]2[N:23]([CH:24]=[CH:25][N:26]=2)[C:16]=1[OH:18]

Participants

5

Reactant 3

HCID 7622TributylamineHCID 821402-AminoimidazoleHCID 2782662Propanedioic acid, 2-(2,4,6-trifluorophenyl)-, 1,3-diethyl ester

Product 1

HCID 178517381HCID 178517381, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of diethyl 2-(2,4,6-trifluorophenyl)malonate (U.S. Pat. No. 6,156,925) (870 mg, 3.0 mmol), 2-aminoimidazole (Hel. Acta. Chim. 76, 2066 (1993)) (274 mg, 3.3 mmol), and 1.0 mL of tributylamine is stirred under nitrogen atmosphere at 160° C. for 0.5 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 (×3) and saturated sodium chloride, dried over magnesium sulfate, and concentrated. The residue is dissolved in ethyl acetate (5 mL) and to this solution is added hexanes (50 mL). The precipitates are collected by filtration, washed with hexanes to give 6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine-5,7-diol as a tan solid (180 mg). MS: m/z 279.9(M−H).

Workup

  1. washthe organic layer is washed with 1.0 N hydrochloric acide (×3) and saturated sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in ethyl acetate (5 mL) and to this solution
  5. additionis added hexanes (50 mL)
  6. filtrationThe precipitates are collected by filtration
  7. washwashed with hexanes

Sources & evidence

ORD record
ord-1b54459249564ee8ae7e05f3194fa109
Source dataset
uspto-grants-2007_10
Patent number
US07285555B2

Reaction notes

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