Phosphorus oxychloride → 4-chloro-7-(methyloxy)-5-(tetrahydro-2H-pyran-4-yloxy)quinazoline

HRID 871396Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[NH:8][CH:9]=[N:10]2)=[C:5]([O:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:4]=1.O=P(Cl)(Cl)[Cl:23].C(N(CC)C(C)C)(C)C>C(Cl)CCl>[Cl:23][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[O:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:10]=[CH:9][N:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7-methoxy-5-(tetrahydro-2H-pyran-4-yloxy)quinazolin-4(3H)-one (0.60 g, 2.17 mmol), POCl3 (0.5 mL), and N,N-diisopropylethylamine (1.5 mL) in ClCH2CH2Cl (6 mL) was heated at 100° C. for 4 hours. After the solvent and reagents were evaporated under reduced pressure, toluene was added to the residue, and the solution was evaporated under reduced pressure. The residue was dried under vacuum to afford 4-chloro-7-methoxy-5-(tetrahydro-2H-pyran-4-yloxy)quinazoline as a brown solid. LC-MS (ESI) m/z 295 (M+H)+.

Workup

customAfter the solvent and reagents were evaporated under reduced pressure, toluene
additionwas added to the residue
customthe solution was evaporated under reduced pressure
customThe residue was dried under vacuum

Sources & evidence

ORD record: ord-8dd51422b9f548d2a1fe3af8572a92b8
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969587B2

Reaction notes

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