Sodium hydride → 6-Methoxy-7-(2-methoxyethoxy)-4-(5-(4-methoxyphenyl)pyrazol-3-yloxy)quinazoline

HRID 855702Notes

Reaction equation

HRID 855702 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH2:31][C:30](=[O:32])[NH:29][N:28]=2)=[CH:23][CH:22]=1.[H-].[Na+]>CN(C=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])[N:5]=[CH:4][N:3]=[C:2]2[O:32][C:30]1[CH:31]=[C:27]([C:24]2[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[NH:28][N:29]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6053665-(4-Methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-oneHCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline

Product 1

HCID 98023396-Methoxy-7-(2-methoxyethoxy)-4-(5-(4-methoxyphenyl)pyrazol-3-yloxy)quinazolineYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using an analogous procedure to that described for Example 9, 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (134 mg, 0.5 mmol), (prepared as described for the starting material in Example 4), was reacted with 3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-5-one (190 mg, 1 mmol) in the presence of sodium hydride (40 mg, 1 mmol, prewashed with THF) in DMF (3 ml) to give 6-methoxy-7-(2-methoxyethoxy)-4-(5-(4-methoxyphenyl)pyrazol-3-yloxy)quinazoline (125 mg, 59%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-ce10a40e79c14fea9f7a4e7b7c23b3b6
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

Loading…