(E)-4-morpholino-2-buten-1-ol → 4-Methylthio-7-[(e)-4-morpholinobut-2-en-1-yloxy]quinazoline

HRID 1782062Notes

Reaction equation

HRID 1782062 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7]/[CH:8]=[CH:9]/[CH2:10][OH:11])[CH2:3][CH2:2]1.O[C:13]1[CH:22]=[C:21]2[C:16]([C:17]([S:23][CH3:24])=[N:18][CH:19]=[N:20]2)=[CH:15][CH:14]=1>>[CH3:24][S:23][C:17]1[C:16]2[C:21](=[CH:22][C:13]([O:11][CH2:10]/[CH:9]=[CH:8]/[CH2:7][N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:14][CH:15]=2)[N:20]=[CH:19][N:18]=1

Participants

3

Reactant 2

HCID 22478312(E)-4-morpholino-2-buten-1-olHCID 1356740197-Hydroxy4-methylsulphanylquinazoline

Product 1

HCID 226492714-Methylthio-7-[(e)-4-morpholinobut-2-en-1-yloxy]quinazolineYield 55.6%

Procedure

Using an analogous procedure to that described in the second last paragraph of Note [12] above, (E)-4-morpholinobut-2-en-1-ol (J. Med. Chem., 1972, 15 110-112; 1.27 g), was reacted with 7-hydroxy-4-methylthioquinazoline (1.2 g) to give 4-methylthio -7-[(E)-4-morpholinobut-2-en-1-yloxy]quinazoline (1.15 g); NMR Spectrum: (CDCl3) 2.45 (br s, 4H), 2.7 (s, 3H), 3.05 (d, 2H), 3.7 (t, 4H), 4.7 (d, 2H), 5.9 (m, 2H), 7.15-7.25 (m, 2H), 7.95 (d, 1H), 8.9 (d, 1H); Mass Spectrum: M+H+ 332.

Sources & evidence

ORD record
ord-0554dbf9a47943f5b233eaed385f3459
Source dataset
uspto-grants-2009_03
Patent number
US07498335B2

Reaction notes

Loading…