1,2-Dibromoethane → 6-(2-Bromoethoxy)-4-(3'-methylanilino)quinazoline

HRID 52042Notes

Reaction equation

HRID 52042 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1.[Br:20][CH2:21][CH2:22]Br>CC(N(C)C)=O>[Br:20][CH2:21][CH2:22][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1

Participants

4

Reactant 2

HCID 78391,2-DibromoethaneHCID 199632076-Hydroxy-4-(3'-methylanilino)quinazoline

Product 1

HCID 199631386-(2-Bromoethoxy)-4-(3'-methylanilino)quinazolineYield 47%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

Using an analogous procedure to that described in Example 39, except that DMA was used in place of DMF and that the reaction mixture was heated to 80° C. for 4 hours, 6-hydroxy-4-(3'-methylanilino)quinazoline was reacted with 1,2-dibromoethane to give 6-(2-bromoethoxy)-4-(3'-methylanilino)quinazoline in 47% yield, m.p. 129°-135° C.

Sources & evidence

ORD record
ord-930a70d401ed49c78d587729df046742
Source dataset
uspto-grants-1997_04
Patent number
US05616582

Reaction notes

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