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

HRID 1708421Notes

Reaction equation

HRID 1708421 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

5

Reactant 3

HCID 105532-Methyl-2-buteneHCID 25134Boron tribromideHCID 178440100HCID 178440100, compound

Product 1

HCID 178440015HCID 178440015, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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.

Sources & evidence

ORD record
ord-d58bd3b2f8d5458f81ad41af3da4400c
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

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