Phosphorus oxychloride → 4-Chloro-7-methoxy-6-(3-(methylsulfonyl)propoxy)quinazoline

HRID 871326Notes

Reaction equation

HRID 871326 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:20][CH3:21])=[C:9]([O:12][CH2:13][CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=2)[N:5]=[CH:4][N:3]=1.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:20][CH3:21])=[C:9]([O:12][CH2:13][CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486872HCID 178486872, compound

Product 1

HCID 866535064-Chloro-7-methoxy-6-(3-(methylsulfonyl)propoxy)quinazolineYield 65%

Procedure

The intermediate 4-hydroxy-7-methoxy-6-(3-(methylsulfonyl)propoxy)quinazoline (700 mg, 2.24 mmol) from the previous step was reacted with POCl3 in the manner described in Example 4A Step 2 to give 4-chloro-7-methoxy-6-(3-(methylsulfonyl)propoxy)quinazoline (480 mg, 1.45 mmol, 65%). LC-MS (ESI) m/z 331 (M+H)+.

Sources & evidence

ORD record
ord-f3c5a096087e4c2da73ba886066e13eb
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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