Sodium hydride → 7-Benzyloxy-4-(4-chloro-2,6-difluoroanilino)-6-methoxyquinazoline

HRID 346570Notes

Reaction equation

HRID 346570 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:29]=[C:28]([F:30])[C:26]([NH2:27])=[C:25]([F:31])[CH:24]=1.[H-].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:27][C:26]3[C:28]([F:30])=[CH:29][C:23]([Cl:22])=[CH:24][C:25]=3[F:31])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15125184-Chloro-2,6-DifluoroanilineHCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazoline

Product 1

HCID 110590287-Benzyloxy-4-(4-chloro-2,6-difluoroanilino)-6-methoxyquinazolineYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using an analogous procedure to that described for the preparation of the starting material in Example 9, 7-benzyloxy-4-chloro-6-methoxyquinazoline (184 mg, 0.61 mmol), (prepared, for example, as described in WO 97/22596, Example 1, but the free base was generated prior to use), was reacted with 4-chloro-2,6-difluoroaniline (200 mg, 1.22 mmol) in the presence of sodium hydride (60%, 87 mg, 1.4 mmol) in DMF (8 ml) to give 7-benzyloxy-4-(4-chloro-2,6-difluoroanilino)-6-methoxyquinazoline (212 mg, 74%).

Sources & evidence

ORD record
ord-6b0186541e394a28af3f1d08396f1e91
Source dataset
uspto-grants-2007_02
Patent number
US07173038B1

Reaction notes

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