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

HRID 2210021Notes

Reaction equation

HRID 2210021 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. NMR Spectrum: (CD3SOCD3) 2.35 (s, 3H), 3.92 (t, 2H), 4.52 (t, 2H), 6.95 (d, 1H), 7.28 (t, 1H), 7.53 (m, 1H), 7.63 (m, 2H), 7.74 (d, 1H), 7.96 (d, 1H), 8.49 (s, 1H), 9.52 (s, 1H); Elemental Analysis: Found C, 57.5; H, 4.2; N, 11.57 C17H16BrN3O requires C, 57.0; H, 4.5; N, 11.7%.

Sources & evidence

ORD record
ord-698f495ecbf24fb2ab6065d20fc26f38
Source dataset
uspto-grants-1995_10
Patent number
US05457105

Reaction notes

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