Ethyl isocyanate → HCID 10270050, compound

HRID 2183559Notes

Reaction equation

HRID 2183559 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[NH:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]#[N:17])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:20]([N:22]=[C:23]=[O:24])[CH3:21]>C1COCC1>[CH2:20]([NH:22][C:23]([N:13]1[CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[C:9]([C:16]#[N:17])=[C:10]([CH3:15])[NH:11][C:12]1=[O:14])=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 24758Sodium hydrideHCID 22473437HCID 22473437, compound

Product 1

HCID 10270050HCID 10270050, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-(2H)-pyrimidine (2.92 g, 10 mmol) in THF (30 mL) was added 95% sodium hydride (0.30 g, 12 mmol). After gas evolution ceased, ethyl isocyanate (0.44 mL, 12 mmol) was added via syringe. The reaction mixture was stirred for 0.5 h, quenched with water and extracted twice with EtOAc. The combined extracts were washed with 0.5 N aqueous NaOH, with water and with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography (25% to 35% EtOAc/hexane) to give, after evaporation of solvent, 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-1-(2H)-pyrimidinecarboxylic acid, 1-ethyl amide as a colorless solid (2.91 g; 80%): 1H NMR (CDCl3, 400 MHz) δ 8.65 (t, 3H, J=5.3 Hz), 7.91 (s, 1H), 7.39 (m, 1H), 7.35 (m, 1H), 7.21 (m, 1H), 7.15 (d, 1H, J=7.9 Hz), 6.24 (s, 1H), 3.25 (m, 2H), 2.10 (s, 3H), 1.10 (t, 3H, J=7.0 Hz); LC/MS (ES+) 363 (M+H+).

Workup

  1. customquenched with water
  2. extractionextracted twice with EtOAc
  3. washThe combined extracts were washed with 0.5 N aqueous NaOH, with water and with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (25% to 35% EtOAc/hexane)
  7. customto give
  8. customafter evaporation of solvent, 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-1-(2H)-pyrimidinecarboxylic acid, 1-ethyl amide as a colorless solid (2.91 g; 80%)

Sources & evidence

ORD record
ord-63550df1974b4cddaecea8edddea9147
Source dataset
uspto-grants-2005_05
Patent number
US06900214B2

Reaction notes

Loading…