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CAS No. : | 870281-86-0 | MDL No. : | MFCD22124614 |
Formula : | C17H16FN3O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | BNMGOWXQUZHWIO-ZDUSSCGKSA-N |
M.W : | 297.33 | Pubchem ID : | 59841052 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.1 g | With triethylamine In <i>tert</i>-butyl alcohol at 30 - 85℃; for 24 h; | (S)-2-(1 -aminopropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one prepared in example 26 (4.2 g) and t-Butanol (21 mL) were charged into a 100 mL round bottom flask. Triethylamine (3.91 mL) and 6-Chloropurine (2.5 g) were added at 30 00. The resultant reaction mixture was heated to85°C and stirred for 24 hours. The reaction mixture was evaporated completely under reduced pressure at 40°C. The resultant residue was diluted with water (100 mL) and stirred for 30 minutes. The precipitate was filtered and the solid was washed with water (30 mL) and n-Hexane (50 mL) and dried for 1 hour under vacuum. The crude was purified by chromatographyusing Si02 (1 00:200) (solvent MeOH: DCM: TEA:: 5: 94: 1). The eluted fractions were evaporated completely under vacuum. The isolated product was diluted in dichloromethane (100 mL) and the organic layer was washed with brine solution (2x25 mL). The organic layer dried over sodium sulphate (10 g) and evaporated under reduced pressure to yield 3.1 g of Idelalisib as pale yellow solid.Purity: 97.87percent by HPLC; chiral purity: 98.77percent by H PLC |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.5 g | With N-ethyl-N,N-diisopropylamine In <i>tert</i>-butyl alcohol at 85 - 90℃; | Example 6:Preparation of 5-fluoro-3-phenyl-2-[(15)-l-(7H-purin-6-ylamino)propyl]- 4(3H)-quinazolinone [idelalisib] A mixture of 2-(l-aminopropyl)-5-fluoro-3-phenyl-3H-quinazolin-4-one (50 g, 0.17 mole) and 6-bromopurine (37.5 g, 0.18 mole) was taken in tert-butanol (500 mL). To this solution, 43.4 g DIPEA [Ν,Ν,-diisopropylethylamine] was added and the reaction mixture was stirred at 85 °C- 90 °C for 20 to 25 hours. After completion of the reaction, the reaction mixture was concentrated by distillation under vacuum and the residue was dissolved in methanol (500 mL). This solution was slowly added to water (5000 mL) and stirred for next 40 to 60 minutes. The solid was filtered then sucked dried. Finally, the solid was dried at 50 °C- 55 °C under vacuum for 4 to 5 hours to get 5-fluoro-3-phenyl-2-[(15)-l-(7H-purin-6-ylamino)propyl]-4(3H)- quinazolinone (idelalisib) (62.5 g, 89percent molar). |
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