Hydrochloric Acid → HCID 178517557, compound

HRID 2112600Notes

Reaction equation

HRID 2112600 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.Cl.[N:22]1[CH:27]=[CH:26][N:25]=[CH:24][C:23]=1[C:28]([NH2:30])=[NH:29].C(N(CCCC)CCCC)CCC.Cl>>[N:22]1[CH:27]=[CH:26][N:25]=[CH:24][C:23]=1[C:28]1[N:30]=[C:11]([OH:13])[C:10]([C:3]2[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])=[C:16]([OH:18])[N:29]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7622TributylamineHCID 470895Pyrazine-2-carboxamidine hydrochlorideHCID 2782662Propanedioic acid, 2-(2,4,6-trifluorophenyl)-, 1,3-diethyl ester

Product 1

HCID 178517557HCID 178517557, compound

Procedure

A mixture of diethyl 2-(2,4,6-trifluorophenyl)malonate (U.S. Pat. No. 6,156,925)(870 mg, 3.0 mmol), 2-pyrazinecarboxamidine hydrochloride (500 mg, 3.15 mmol), and 600 mg of tributylamine is stirred under nitrogen atmosphere at 180° C. for 1 h and cooled to room temperature. The mixture is cooled to room temperature and treated with 1.0 N hydrochloric acid. The precipitates are collected by filtration, washed with water and dried to give 2-pyrazin-2-yl-5-(2,4,6-trifluorophenyl)pyrimidine-4,6-diol as a tan solid (401 mg), which is used directly in the next step.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationThe precipitates are collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ec86906b1d404b179fa53451e604ccfb
Source dataset
uspto-grants-2009_04
Patent number
US07524849B2

Reaction notes

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