Phosphorus oxychloride → 4-Chloro-6-(3-chloropropoxy)-7-methoxyquinazoline

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[N:12]=[CH:11][N:10]=[C:9]2O.O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:9]1[C:8]2[C:13](=[CH:14][C:15]([O:16][CH3:17])=[C:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])[CH:7]=2)[N:12]=[CH:11][N:10]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 1784868706-(3-chloropropoxy)-7-methoxy-1H-quinazolin-4-one

Product 1

HCID 507422644-Chloro-6-(3-chloropropoxy)-7-methoxyquinazolineYield 86%

Procedure

The intermediate 6-(3-chloropropoxy)-4-hydroxy-7-methoxyquinazoline (3.5 g, 13.0 mmol) was reacted with POCl3 in the manner described in Example 4A Step 2 to give 4-chloro-6-(3-chloropropoxy)-7-methoxyquinazoline (3.2 g, 11.2 mmol, 86%). LC-MS (ESI) m/z 287 (M+H)+.

Sources & evidence

ORD record: ord-a766e46a82834776bc206a14e21063f1
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09320739B2

Reaction notes

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