Hydrogen Bromide → HCID 178441656, compound

HRID 1655566Notes

Reaction equation

HRID 1655566 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[NH:29][N:28]=[N:27][N:26]=3)=[CH:15][CH:14]=2)[C:8]([CH2:30]Br)=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].Br.[CH3:33][O-:34].[Na+]>C(O)(=O)C.CO>[CH2:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[NH:29][N:28]=[N:27][N:26]=3)=[CH:15][CH:14]=2)[C:8]([CH2:30][O:34][CH3:33])=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 10942334Sodium MethoxideHCID 178441600HCID 178441600, compound

Product 1

HCID 178441656HCID 178441656, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

2-n-Butyl-5-hydroxymethyl-4-{N-[(2-1H-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}pyrimidine hydrochloride, the product of Example 2B, is converted to 2-butyl-5-bromomethyl-4-{N-[(2'-[1H-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}pyrimidine by treatment with hydrogen bromide in acetic acid according to the method of A. Schellenberger and K. Winter in Z. Physiol. Chem., 322, 164 (1960). The bromomethyl intermediate is then converted to the title compound by treatment with sodium methoxide in methanol.

Sources & evidence

ORD record
ord-ce180b08491e4469ab2a8adee0ddc5ef
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

Loading…