Ethyl 3-oxovalerate → 2-(3-chlorophenyl)-6-ethylpyrimidin-4(3H)-one

HRID 1508671Notes

Reaction equation

HRID 1508671 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](=[NH:7])[NH2:6].O=[C:12]([CH2:19][CH3:20])[CH2:13][C:14](OCC)=[O:15].C[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:6][C:14](=[O:15])[CH:13]=[C:12]([CH2:19][CH3:20])[N:7]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 78656Ethyl 3-oxovalerateHCID 2041443-Chloro-benzamidineHCID 10942334Sodium Methoxide

Product 1

HCID 1356311952-(3-chlorophenyl)-6-ethylpyrimidin-4(3H)-oneYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1-L round bottomed flask was charged with 3-chlorobenzimidamide (23.9 g, 154 mmol, 1 eq.), ethyl 3-oxopentanoate (27.8 g, 193 mmol, 1.25 eq.), and ethanol (500 mL). To the mixture was added sodium methoxide (10.0 g, 185 mmol, 1.20 eq.). The resulting mixture was stirred under reflux for 20 hr. After cooling to room temperature, the mixture was evaporated under reduced pressure to 50 mL. The residual slurry was cautiously treated with 2N HCl (219 mL). Solid was collected by filtration and washed with water followed by ether to afford 2-(3-chlorophenyl)-6-ethylpyrimidin-4(3H)-one (9.3 g, 39% yield), which was carried forward into the next step without further purification. 1H NMR (CD3OD, 500 MHz) δ 8.07 (s, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.62-7.58 (m, 1H), 7.52 (t, J=8.0, Hz, 1H), 6.27 (s, 1H), 2.66 (q, J=7.5 Hz, 2H), 1.29 (t, J=7.5 Hz, 3H).

Workup

  1. temperatureunder reflux for 20 hr
  2. customthe mixture was evaporated under reduced pressure to 50 mL
  3. additionThe residual slurry was cautiously treated with 2N HCl (219 mL)
  4. filtrationSolid was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-551c6cbdc10d4da1b0cad0385f179416
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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