Pyrazine-2-carboxamidine hydrochloride → HCID 178517556, compound

HRID 2112610Notes

Reaction equation

HRID 2112610 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.Cl.[N:26]1[CH:31]=[CH:30][N:29]=[CH:28][C:27]=1[C:32]([NH2:34])=[NH:33]>C(N(CCCC)CCCC)CCC>[CH:1]1([C:8]2[N:34]=[C:32]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][N:26]=3)[N:33]=[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

4

Reactant 2

HCID 470895Pyrazine-2-carboxamidine hydrochlorideHCID 67047753HCID 67047753, compound

Product 1

HCID 178517556HCID 178517556, compound

Reagents, catalysts & solvents 1

HCID 7622TributylamineSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of ethyl 3-cycloheptyl-3-oxo-2-(2,4,6-trifluorophenyl)propanoate (649 mg, 1.9 mmol) and 2-pyrazinecarboxamidine hydrochloride (452 mg, 2.85 mmol) in 1.5 mL of tributylamine is stirred under nitrogen atmosphere at 160° C. for 4 h. The mixture is cooled to room temperature and the excess of tributylamine is decanted off. The residue is washed with hexanes and chromatographed over silica gel, eluting with 10% methanol in ethyl acetate. Concentration provides 6-cycloheptyl-2-pyrazin-2-yl-5-(2,4,6-trifluorophenyl)pyrimidin-4-ol as a light yellow solid. MS: m/z 401.2 (M+H).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customthe excess of tributylamine is decanted off
  3. washThe residue is washed with hexanes
  4. customchromatographed over silica gel
  5. washeluting with 10% methanol in ethyl acetate
  6. concentrationConcentration

Sources & evidence

ORD record
ord-cd2be231e3124491915bf4cb88d9fed5
Source dataset
uspto-grants-2009_04
Patent number
US07524849B2

Reaction notes

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