Lithium iodide → 2-(2,6-Dichloro-4-pyridyl)-5,6-diethyl-3-propargyl-5,6-dihydropyrimidin-4-one

HRID 1779893Notes

Reaction equation

HRID 1779893 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:13]([CH2:14][C:15]#[CH:16])[C:12](=[O:17])[C:11]([CH2:22][CH3:23])(C(OC)=O)[CH:10]([CH2:24][CH3:25])[N:9]=2)[CH:5]=[C:4]([Cl:26])[N:3]=1.[I-].[Li+]>N1C=CC=CC=1>[Cl:26][C:4]1[CH:5]=[C:6]([C:8]2[N:13]([CH2:14][C:15]#[CH:16])[C:12](=[O:17])[CH:11]([CH2:22][CH3:23])[CH:10]([CH2:24][CH3:25])[N:9]=2)[CH:7]=[C:2]([Cl:1])[N:3]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 190485482-(2,6-Dichloro-4-pyridyl)-5,6-diethyl-5-methoxycarbonyl-3-propargyl-5,6-dihydropyrimidin-4-one

Product 1

HCID 190485452-(2,6-Dichloro-4-pyridyl)-5,6-diethyl-3-propargyl-5,6-dihydropyrimidin-4-oneYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 5.0 g (12.6 mmol) of 2-(2,6-dichloro-4-pyridyl)-5,6-diethyl-5-methoxycarbonyl-3-propargyl-5,6-dihydropyrimidin-4-one in 50 mL of pyridine was added 11.5 g (76 mmol) of lithium iodide and refluxed overnight. The reaction was cooled to room temperature, quenched onto 250 mL of water andextracted with EtOAc (2×300 mL). The organics were combined, washed with water (1×200 mL), dilute HCl (2×200 mL), water (1×200 mL), dilute sodium bisulfite (1×200 mL) and saturated sodium chloride (1×200 mL). The EtOAc was diluted with 600 mL of hexanes and vacuum filtered through a pad of silica gel. The filtrate was dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The residue was triturated with diethyl ether and solid impurities removed by filtration. The filtrate was once again evaporated to dryness in vacuo to give 2.2 g (5.75 mmol, 46%) of desired product as an oil.

Workup

  1. temperaturerefluxed overnight
  2. customquenched onto 250 mL of water
  3. washwashed with water (1×200 mL), dilute HCl (2×200 mL), water (1×200 mL), dilute sodium bisulfite (1×200 mL) and saturated sodium chloride (1×200 mL)
  4. additionThe EtOAc was diluted with 600 mL of hexanes and vacuum
  5. filtrationfiltered through a pad of silica gel
  6. dry with materialThe filtrate was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. customThe residue was triturated with diethyl ether and solid impurities
  10. customremoved by filtration
  11. customThe filtrate was once again evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-3f097c0aec4844b9b3300cdb2b5cb9c8
Source dataset
uspto-grants-1997_05
Patent number
US05629264

Reaction notes

Loading…