Trifluoroacetic acid → HCID 131717223, compound

HRID 2372859Notes

Reaction equation

HRID 2372859 reaction equation
N[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH2:9][CH2:10][CH2:11][CH3:12])[N:3]=1.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([O:29]C(C)(C)C)=[O:28])=[CH:17][CH:16]=1.[NH+]1C=CC=NC=1.[OH-].[Na+].FC(F)(F)C(O)=[O:45]>CN(C=O)C.CO>[CH2:9]([CH:4]1[NH:3][C:2](=[O:45])[CH:7]=[C:6]([CH3:8])[N:5]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([OH:29])=[O:28])=[CH:17][CH:16]=1)[CH2:10][CH2:11][CH3:12]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 199022284-Amino-2-n-butyl-6-methylpyrimidineHCID 21791174HCID 21791174, compound

Product 1

HCID 131717223HCID 131717223, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Heating 4-amino-2-n-butyl-6-methylpyrimidine (from Example 27) 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 of the carboxyl group, provides the title compound.

Sources & evidence

ORD record
ord-bbbc3646665b42b2a1169ea580df9032
Source dataset
uspto-grants-1992_03
Patent number
US05100897

Reaction notes

Loading…