Ethanol → HCID 18444274, compound

HRID 459863Notes

Reaction equation

HRID 459863 reaction equation
C([OH:3])C.Cl.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]2[N:20]=[C:19]([C:21]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[O:22])[CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].[Cl:29][C:30]1[N:35]=[C:34](Cl)[CH:33]=[CH:32][N:31]=1>C(N(CC)CC)C>[OH2:3].[Cl:29][C:30]1[N:35]=[C:34]([N:26]2[CH2:25][CH2:24][N:23]([C:21]([C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([C:9]4[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=4)[N:20]=3)=[O:22])[CH2:28][CH2:27]2)[CH:33]=[CH:32][N:31]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 775312,4-DichloropyrimidineHCID 22930986HCID 22930986, compound

Product 1

HCID 18444274HCID 18444274, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

To an ethanol (6 ml) solution of 327 mg of 1-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazine monohydrochloride were added 0.28 ml of triethylamine and 148 mg of 2,4-dichloropyrimidine, followed by 2 hours of stirring at an oil bath temperature of 90° C. After the solvent was evaporated, water was added thereto, followed by extraction with chloroform. The organic layer was washed with water and then dried over anhydrous magnesium sulfate, and thereafter, the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) and further, recrystallization was carried out from acetonitrile-diisopropyl ether to obtain 70 mg of 2-chloro-4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}pyrimidine monohydrate as colorless crystals.

Workup

  1. customAfter the solvent was evaporated
  2. additionwater was added
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  8. customfurther, recrystallization

Sources & evidence

ORD record
ord-90e31408fb57475f88da61e79e40f77f
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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