Phosphorus oxychloride → 4-Chloro-6-fluoro-7-morpholin-4-ylquinazoline

HRID 2274153Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[N:8]=[CH:7][NH:6][C:5]2=O.P(Cl)(Cl)([Cl:21])=O.C(N(C(C)C)C(C)C)C>>[Cl:21][C:5]1[C:4]2[C:9](=[CH:10][C:11]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[C:2]([F:1])[CH:3]=2)[N:8]=[CH:7][N:6]=1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 81531Diisopropylethylamine

HCID 1360002446-fluoro-7-morpholin-4-yl-3H-quinazolin-4-one

Product 1

HCID 772309324-Chloro-6-fluoro-7-morpholin-4-ylquinazolineYield 123.3%

Procedure

5.0 g (0.02 mol) of 6-fluoro-7-morpholin-4-yl-3H-quinazolin-4-one were suspended in 37.0 ml (0.04 mol) of phosphoryl chloride at room temperature, 3.4 ml (0.02 mol) of N-ethyldiisopropylamine were subsequently added, and the mixture was heated under reflux for 2 h. Conventional work-up gave 6.6 g of 4-chloro-6-fluoro-7-morpholin-4-ylquinazoline.

Workup

temperaturethe mixture was heated
temperatureunder reflux for 2 h

Sources & evidence

ORD record: ord-a041d9deafcc4cb6882fded8174b136e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126952B2

Reaction notes

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