2-Methyl-2-butene → HCID 178440015, compound

Reaction equation

[CH2:1]([C:4]1[N:9]=[C:8]([CH2:10]COC)[N:7]2[NH:14][C:15](=[O:17])[N:16]=[C:6]2[C:5]=1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:35][N:34]=[N:33][N:32]=2)=[CH:21][CH:20]=1)[CH2:2][CH3:3].CC=C(C)C.B(Br)(Br)[Br:42]>C(Cl)(Cl)Cl>[CH2:1]([C:4]1[N:9]=[C:8]([CH2:10][Br:42])[N:7]2[NH:14][C:15](=[O:17])[N:16]=[C:6]2[C:5]=1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:35][N:34]=[N:33][N:32]=2)=[CH:21][CH:20]=1)[CH2:2][CH3:3]

Participants

Procedure

1 g of 7-n-propyl-5-methoxyethyl-8-{[2 '- (5-tetrazolyl)-4-biphenylyl]methyl}-1,2,4-triazolo[1,5-c]pyrimidin-2 (3H) -one, prepared in Example 169, are dissolved in 50 ml of chloroform stabilised with amylene. 0.7 ml of boron tribromide is added and the mixture is stirred for 8 hours at room temperature; the derivative 7-n-propyl-5-bromomethyl-8-{[2 '- (5-tetrazolyl ) -4-biphenylyl]methyl}-1,2,4-triazolo[1,5-c]pyrimidin-2(3H )-one thereby formed is taken up with dilute sodium hydroxide solution and stirred again for 6 hours. The aqueous phase is then separated after settling has taken place and acidified by bubbling in sulphur dioxide, and the crystals formed are drained, washed with acetone and then dried to give 0.6 g of 7-n-Propyl-5-hydroxymethyl-8-{[2'-(5 -tetrazolyl ) - 4 -biphenylyl ]methyl }- 1,2,4 -triazolo [ 1,5-c]pyrimidin-2(3H)-one in the form of crystals of melting point 182°-183° C.