Methylamine → 5-Hydroxy-1-methyl-6-oxo-2-(1-phenyl-cyclopentylmethyl)-1,6-dihydro-pyrimidine-4-carboxylic acid methylamide

HRID 1409561Notes

Reaction equation

HRID 1409561 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

Reactant 2

HCID 6329MethylamineHCID 867102605-Hydroxy-1-methyl-6-oxo-2-(1-phenyl-cyclopentylmethyl)-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 867102625-Hydroxy-1-methyl-6-oxo-2-(1-phenyl-cyclopentylmethyl)-1,6-dihydro-pyrimidine-4-carboxylic acid methylamideYield 24%

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+).

Workup

  1. additionwas added a catalytic amount of Me3AI under argon atmosphere in a sealed tube
  2. customAfter completion of the reaction, it
  3. customwas quenched with ice slowly
  4. extractionextracted with EtOAc
  5. washThe combined organic layer was then washed with water and brine
  6. dry with materialIt was then dried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-7bf33e3fbce74518909f7d81eb48985a
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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