Trifluoroacetic acid → 2-n-Butyl-1-(2'-carboxybiphen-4-yl)methyl-5,6-dimethylpyrimidin-4(3H)-one

HRID 2372858Notes

Reaction equation

HRID 2372858 reaction equation
N[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([CH2:10][CH2:11][CH2:12][CH3:13])[N:3]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([O:30]C(C)(C)C)=[O:29])=[CH:18][CH:17]=1.[NH+]1C=CC=NC=1.[OH-].[Na+].FC(F)(F)C(O)=[O:46]>CN(C=O)C.CO>[CH2:10]([CH:4]1[NH:3][C:2](=[O:46])[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([OH:30])=[O:29])=[CH:18][CH:17]=1)[CH2:11][CH2:12][CH3:13]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 199022354-Amino-2-n-butyl-5,6-dimethylpyrimidineHCID 21791174HCID 21791174, compound

Product 1

HCID 1317172222-n-Butyl-1-(2'-carboxybiphen-4-yl)methyl-5,6-dimethylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Heating 4-amino-2-n-butyl-5,6-dimethylpyrimidine (from Example 23) with 4-bromomethyl-2'-t-butoxycarbonylbiphenyl in an appropriate solvent such as methanol or DMF, followed by treatment of the intermediate pyrimidinium species with aqueous base such as 0.1N sodium hydroxide as described by Brown, Hoerger, and Mason (J. Chem. Soc., 1955, 4035), followed by treatment with neat trifluoroacetic acid to achieve final deprotection for the carboxyl group, would provide the title compound.

Sources & evidence

ORD record
ord-a354a3fc9ede4077ab7a1788ba6a846b
Source dataset
uspto-grants-1992_03
Patent number
US05100897

Reaction notes

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