4-Methoxybenzyl alcohol → 7-Bromo-4-(4-methoxybenzyloxy)quinazoline

HRID 2274143Notes

Reaction equation

HRID 2274143 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[H-].[Na+].[Br:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](Cl)=[N:19][CH:20]=[N:21]2)=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([O:8][CH2:7][C:6]3[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[N:19][CH:20]=[N:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 167808557-Bromo-4-chloroquinazoline

Product 1

HCID 674019877-Bromo-4-(4-methoxybenzyloxy)quinazolineYield 34.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

226.0 g (01.64 mol) of 4-methoxybenzyl alcohol in 0.5 l of toluene were added dropwise to a suspension of 80.0 g (2.0 mol) of sodium hydride [60% in paraffin oil] in 3.0 l of toluene between 15° C. and 20° C. The mixture was subsequently stirred at room temperature for a further 1 h. 165.9 g (1.64 mol) of 7-bromo-4-chloroquinazoline were then added in portions, and the reaction mixture was stirred for 48 h. Conventional work-up gave 194.8 g of 7-bromo-4-(4-methoxybenzyloxy)quinazoline as solid.

Workup

  1. stirringthe reaction mixture was stirred for 48 h

Sources & evidence

ORD record
ord-ac47c607a0f84fa3a0640f5458d650c9
Source dataset
uspto-grants-2015_09
Patent number
US09126952B2

Reaction notes

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