Iodoethane → HCID 178437571, compound

HRID 1779891Notes

Reaction equation

HRID 1779891 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:9][CH:10]([CH2:19][CH3:20])[CH:11]([C:15]([O:17][CH3:18])=[O:16])[C:12](=[O:14])[N:13]=2)[CH:5]=[C:4]([Cl:21])[N:3]=1.[CH3:22][C:23](C)([O-])C.[K+].ICC>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:9][CH:10]([CH2:19][CH3:20])[C:11]([CH2:22][CH3:23])([C:15]([O:17][CH3:18])=[O:16])[C:12](=[O:14])[N:13]=2)[CH:5]=[C:4]([Cl:21])[N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 23665647Potassium tert-butoxideHCID 178437572HCID 178437572, compound

Product 1

HCID 178437571HCID 178437571, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 27.0 g (81.8 mmol) of 2-(2,6-dichloro-4-pyridyl)-6-ethyl-5-methoxycarbonyl5,6-dihydropyrimidin-4-one in 500 mL of dimethylformamide was added at 0° C. over 30 min via a solid addition funnel 19.3 g (172 mmol) of potassium-t-butoxide followed by the dropwise addition over 15 min of 13.3 g (85.2 mmol) of iodoethane. The reaction was stirred at 0° C. for one hour before quenching onto 700 mL of ice water. The aqueous was acidified to pH=1 (conc. HCl) and extracted with EtOAc (3×400 mL). The organics were combined before washing with water (2×500 mL), and saturated NaCl (1×300 mL) drying over MgSO4, filtering and evaporating to dryness in vacuo to give 27.32 g (76.3 mmol, 93%) of the desired product as a pale yellow solid with mp=202°-203° C.

Workup

  1. custombefore quenching onto 700 mL of ice water
  2. extractionextracted with EtOAc (3×400 mL)
  3. washbefore washing with water (2×500 mL), and saturated NaCl (1×300 mL)
  4. dry with materialdrying over MgSO4
  5. filtrationfiltering
  6. customevaporating to dryness in vacuo

Sources & evidence

ORD record
ord-0684e6d9766d4c36ab3176f3e79b380a
Source dataset
uspto-grants-1997_05
Patent number
US05629264

Reaction notes

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