Triethylamine → HCID 86686656, compound

HRID 1464959Notes

Reaction equation

HRID 1464959 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:7][C:8]=1[CH3:9].[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[CH:21][N:20]=1.C(N(CC)CC)C>O1CCOCC1>[Cl:18][C:19]1[N:20]=[CH:21][N:22]=[C:23]([N:15]2[CH2:14][CH2:13][N:12]([C:10]([C:5]3[CH:6]=[CH:7][C:8]([CH3:9])=[C:3]([F:2])[CH:4]=3)=[O:11])[CH2:17][CH2:16]2)[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 45791551(3-Fluoro-4-methylphenyl)(piperazin-1-yl)methanone hydrochloride

Product 1

HCID 86686656HCID 86686656, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (3-fluoro-4-methylphenyl)(piperazin-1-yl)methanone hydrochloride (434 mg, 1.67 mmol), 4,6-dichloropyrimidine (250 mg, 1.67 mmol), and triethylamine (0.94 mL, 6.71 mmol) in dioxane (10 mL) was reflexed with stirring for 4 h. After cooling to rt, the mixture was poured onto water, and the aqueous phase was extracted with EtOAc (twice). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (5:1-2:1) to give 400 mg (71% yield) of the title compound as a white solid.

Workup

  1. additionthe mixture was poured onto water
  2. extractionthe aqueous phase was extracted with EtOAc (twice)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (5:1-2:1)

Sources & evidence

ORD record
ord-7de4d4307a5f4b718a214d8bf42f304f
Source dataset
uspto-grants-2015_04
Patent number
US08999974B2

Reaction notes

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