3,5-Dimethylpyrazole → HCID 11848914, compound

HRID 889103Notes

Reaction equation

HRID 889103 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:19][C:20]1[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=1>C(#N)C>[CH3:19][C:20]1[CH:24]=[C:23]([CH3:25])[N:22]([C:2]2[N:11]=[C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[N:21]=1

Participants

4

Reactant 2

HCID 62103,5-DimethylpyrazoleHCID 3179082-chloro-N-phenylquinazolin-4-amine

Product 1

HCID 11848914HCID 11848914, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

(2-Chloro-quinazolin-4-yl)-phenyl amine (250 mg, 0.98 mmol) was dissolved in acetonitrile (4 mL) and 3,5-dimethylpyrazole (140 mg, 1.47 mmol) was added. The mixture was heated in a sealed tube at 130° C. for 12 hours. The mixture was concentrated and the residue basified with sodium hydrogencarbonate, extracted with chloroform dried over anhydrous sodium sulfate filtrated and evaporated. The crude product was purified by column chromatography (ethylacetate/hexane) to give [2-(3,5-dimethyl-pyrazol-1-yl)-quinazolin-4-yl]-phenyl-amine (150 mg, 49%). Mp. 262.4-265.3° C.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with chloroform
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. customevaporated
  6. customThe crude product was purified by column chromatography (ethylacetate/hexane)

Sources & evidence

ORD record
ord-61d7a5841e1045afbac5be3a1abaf7c9
Source dataset
uspto-grants-2012_08
Patent number
US08252806B2

Reaction notes

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