Isopropanol → HCID 69330375, compound

HRID 1292732Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8](P(C)(C)=O)=[C:9]([OH:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[P].[CH3:18][CH:19]([OH:21])C>>[NH:5]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:19](=[O:21])[CH3:18])[CH:10]=2)[N:5]=[CH:4][N:3]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Reactant 3

HCID 3776Isopropanol

HCID 5462309Phosphorus

HCID 86594159HCID 86594159, compound

Product 1

HCID 69330375HCID 69330375, compound

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-chloro-7-dimethylphosphinyl-6-quinazolinol, acetate ester (See e.g. PCT lnt. Appl.(2001) WO 0104102 for the 7-methoxy analog and subsequent examples below for conversion of quinazinols to triflates followed by displacement with “J”, our phosphorus-containing moiety) (3.2 mmol) and 3-chloro-4-flluoro aniline (3.3 mmol) in 2-propanol (20 mL) is heated at 90° C. for 10 hr. After this time the reaction mixture is cooled and the resulting product recovered to afford the 4-anilino-6-acetoxy quinazoline product. This material is then treated with MeOH (17 mL) followed by concentrated ammonium hydroxide and the resulting solution stirred for 17 h. After this time the reaction mixture is evaporated and the residue chromatographed on silica gel (10% MeOH/DCM) to afford deacetylated product.

Workup

temperatureAfter this time the reaction mixture is cooled
customthe resulting product recovered

Sources & evidence

ORD record: ord-9e7a52ab48bc499cb1791a3e483c09fb
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238679B2

Reaction notes

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