POCl3 Chlorination of 4-Quinazolones

Journal of Organic Chemistry

Volumn 76, Issue 6, 2011, Pages 1653-1661

  Arnott, Euan A ^a   Chan, Lai C ^a   Cox, Brian G ^a   Meyrick, Brian ^a   Phillips, Andy ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BASIC CONDITIONS; KINETIC ANALYSIS; MULTIPLE SUBSTITUTIONS; PHOSPHORYLATION REACTIONS; PRODUCT FORMATION; REACTION PROFILE; TIME-SCALES;

PHOSPHORUS; PHOSPHORYLATION;

REACTION INTERMEDIATES;

4 CHLORO 5,7 DIFLUOROQUINAZOLINE; 4(3H) QUINAZOLINONE DERIVATIVE; CHLORINE DERIVATIVE; CHLOROQUINAZOLINE; DIMER; PHOSPHORUS; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; PHOSPHATE; PHOSPHORUS DERIVATIVE; PHOSPHORUS OXYCHLORIDE;

ARTICLE; CHLORINATION; CONTROLLED STUDY; DRUG SYNTHESIS; FLUORINE NUCLEAR MAGNETIC RESONANCE; HEATING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PHOSPHORYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SUBSTITUTION REACTION; TEMPERATURE DEPENDENCE; CHEMISTRY; DIMERIZATION; HALOGENATION; KINETICS;

DIMERIZATION; HALOGENATION; KINETICS; PHOSPHATES; PHOSPHORUS COMPOUNDS; PHOSPHORYLATION; QUINAZOLINES;

EID: 79953836131     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102262k     Document Type: Article

References (8)

1. Noble, M. E. M.; Endicott, J. A.; Johnson, L. N. Science 2004, 303, 1800.
2. Armarego, W. L. F. The Chemistry of Heterocyclic Compounds, 24, Fused Pyrimidines: Part 1: Quinazolines; Wiley-Interscience: New York, 1967.
3. Robins, M. J.; Uznański, B. Can. J. Chem. 1981, 59 (17), 2601.
4. Anderson, N. G.; Ary, T. D.; Berg, J. L.; Bernot, P. J.; Chan, Y. Y.; Chen, C.-K.; Davies, M. L.; DiMarco, J. D.; Dennis, R. D.; Deshpande, R. P.; Do, H. D.; Droghini, R.; Early, W. A.; Gougoutas, J. Z.; Grosso, J. A.; Harris, J. C.; Haas, O. W.; Jass, P. A.; Kim, D. H.; Kodersha, G. A.; Kotnis, A. S.; LaJeunesse, J.; Lust, D. A.; Madding, G. D.; Modi, S. P.; Moniot, J. L.; Nguyen, A.; Palaniswamy, V.; Phillipson, D. W.; Simpson, J. H.; Thoraval, D.; Thurston, D. A.; Tse, K.; Polomski, R. E.; Wedding, D. L.; Winter, W. J. Org. Process Res. Dev. 1997, 1 (4), 300.
5. Tanner, J. E. J. Chem. Phys. 1970, 52, 2523.
6. Grunze, H. Z., Anorg. Allgem. Chem. 1963, 324, 1.
7. pKa values in water from the database ACD/pKa DB and references cited therein.
8. For example, reaction of related 5,7-difluoroquinazolin-4-ol with the less reactive P-Cl species (PhO) 2P(O)Cl forms initially predominantly the (N)-substituted quinazolone, which then equilibrates with the (O)-substituted species ; Pointon, S. Unpublished work.