Methylamine → 5-Hydroxy-1-methyl-6-oxo-2-(1-phenyl-cyclopentylmethyl)-1,6-dihydro-pyrimidine-4-carboxylic acid methylamide
Reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:15][C:16]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:20][CH2:19][CH2:18][CH2:17]2)[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=O)C.[CH3:27][NH2:28]>>[CH3:27][NH:28][C:4]([C:6]1[N:7]=[C:8]([CH2:15][C:16]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:20][CH2:19][CH2:18][CH2:17]2)[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:3]Participants
3
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of 5-hydroxy-1-methyl-6-oxo-2-(1-phenyl-cyclopentylmethyl)-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (175 mg, 0.491 mmol) and methyl amine (0.98 ml, 1.96 mmol, 2M in THF) was added a catalytic amount of Me3AI under argon atmosphere in a sealed tube and it was heated at 60° C. for 16 h. After completion of the reaction, it was quenched with ice slowly and then extracted with EtOAc. The combined organic layer was then washed with water and brine. It was then dried over Na2SO4 and concentrated under vacuum. Purification by preparative HPLC provided the title compound as an off-white solid (40 mg, 24%). LCMS: m/z=342.0 (MH+).