Hydrochloric Acid → HCID 22473459, compound

HRID 2183561Notes

Reaction equation

HRID 2183561 reaction equation
[CH2:1]([NH:3][C:4]([N:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([O:20]C)=[O:19])[CH:13]=2)[C:10]([C:22]#[N:23])=[C:9]([CH3:24])[NH:8][C:7]1=[O:25])=[O:5])[CH3:2].CO.[OH-].[Li+].Cl>O>[CH2:1]([NH:3][C:4]([N:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=2)[C:10]([C:22]#[N:23])=[C:9]([CH3:24])[NH:8][C:7]1=[O:25])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 10154435HCID 10154435, compound

Product 1

HCID 22473459HCID 22473459, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 6-(3-carbomethoxyphenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-1-(2H)-pyrimidinecarboxylic acid, 1-ethyl amide (0.34 g, 1.0 mmol), MeOH (9 mL) and water (3 mL) at 0° C. was added lithium hydroxide (0.84 g, 20.0 mmol). The reaction mixture was stirred for 1 h, acidified to pH 2 with 1 N HCl and extracted with EtOAc. The extract was dried (MgSO4) and concentrated in vacuo to give 6-(3-carboxyphenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-1-(2H)-pyrimidinecarboxylic acid, 1-ethyl amide as a colorless solid (0.30 g, 92%): 1H NMR (MeOH-d4, 400 MHz) δ 8.98 (s, 1H), 7.89 (m, 2H), 7.46 (d, 1H, J=7.5 Hz), 7.42 (t, 1H, J=7.5 Hz), 6.12 (s, 1H), 3.16 (m, 2H), 2.06 (s, 3H), 1.03 (t, 3H, J=7.0 Hz).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extract was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68b3d92dbaf5454c96eecb27b25b998c
Source dataset
uspto-grants-2005_05
Patent number
US06900214B2

Reaction notes

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