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

HRID 1826275
Notes
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Reaction equation

HRID 1826275 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1355106777-(Acetyloxy)-5-[(tetrahydro-2H-pyran-4-yl)oxy]-4(3H)-quinazolinone

Product 1

HCID 221407987-Quinazolinol, 4-chloro-5-[(tetrahydro-2H-pyran-4-yl)oxy]-, 7-acetate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-ef9b3f6fa5074a569914af2edbef27de
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07049438B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes