Phosphorus oxychloride → 7-Quinazolinol, 4-chloro-5-[(tetrahydro-2H-pyran-4-yl)oxy]-, 7-acetate

HRID 1373288Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=O)[NH:10][CH:11]=[N:12]2)=[C:7]([O:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:6]=1)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.P(Cl)(Cl)([Cl:34])=O>ClCCCl>[C:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([Cl:34])=[N:10][CH:11]=[N:12]2)=[C:7]([O:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 7-acetoxy-5-tetrahydropyran-4-yloxy-3,4-dihydroquinazolin-4-one (3.04 g), diisopropylethylamine (4.34 ml), phosphoryl chloride (1.02 ml) and 1,2-dichloroethane (60 ml) was stirred and heated to 80° C. for 2 hours. The mixture was evaporated to give 7-acetoxy-4-chloro-5-tetrahydropyran-4-yloxyquinazoline which was used without further purification.

Workup

customThe mixture was evaporated

Sources & evidence

ORD record: ord-0e52511173744c54a8dbdcf96e226c28
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160891B2

Reaction notes

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