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

HRID 1779892Notes

Reaction equation

HRID 1779892 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]2[NH:11][CH:12]([CH2:23][CH3:24])[C:13]([CH2:21][CH3:22])([C:17]([O:19][CH3:20])=[O:18])[C:14](=[O:16])[N:15]=2)[CH:7]=[C:6]([Cl:25])[N:5]=1.[C:26]1(C)[CH:31]=CC=C[CH:27]=1>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]2[N:15]([CH2:31][C:26]#[CH:27])[C:14](=[O:16])[C:13]([CH2:21][CH3:22])([C:17]([O:19][CH3:20])=[O:18])[CH:12]([CH2:23][CH3:24])[N:11]=2)[CH:7]=[C:6]([Cl:25])[N:5]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24758Sodium hydrideHCID 178437571HCID 178437571, compound

Product 1

HCID 190485482-(2,6-Dichloro-4-pyridyl)-5,6-diethyl-5-methoxycarbonyl-3-propargyl-5,6-dihydropyrimidin-4-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 3.15 g (78 mmol) of sodium hydride in 50 mL of dimethylformamide at 0° C. was added dropwise over 1.5 hr a solution of 26.9 g (75 mmol) of 2-(2,6-dichloro-4-pyridyl)-5,6-diethyl-5-methoxycarbonyl-5,6-dihydropyrimidin-4-one in 200 mL of dimethylformamide. When this addition was complete 12.5 mL (16.73 g, 112.5 mmol) of 80% propargyl brmide in toluene was added and the reaction stirred at room temperature overnight. Upon completion the reaction was quenched onto 600 mL of ice/water, extracted with ethyl acetate (3×400 mL), the organics were combined, washed with water (2×300 mL) and saturated sodium chloride (2×500 mL), dried over Na2SO4, filtered and evaporated to dryness in vacuo to give 29.23 g (73.8 mmol, 98%) of the desired product as a yellow solid.

Workup

  1. additionWhen this addition
  2. additionwas added
  3. customUpon completion the reaction was quenched onto 600 mL of ice/water
  4. extractionextracted with ethyl acetate (3×400 mL)
  5. washwashed with water (2×300 mL) and saturated sodium chloride (2×500 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d51e2041d7dc4a2ebe82d568b763c313
Source dataset
uspto-grants-1997_05
Patent number
US05629264

Reaction notes

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