Propargyl bromide → HCID 15767157, compound

HRID 1768518Notes

Reaction equation

HRID 1768518 reaction equation
[C:1]1([C:7]2[NH:12][C:11](=[O:13])[C:10]3[CH2:14][CH2:15][CH2:16][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:19](Br)[C:20]#[CH:21]>O1CCCC1.C1(C)C=CC=CC=1.C(Cl)Cl>[C:1]1([C:7]2[N:12]([CH2:21][C:20]#[CH:19])[C:11](=[O:13])[C:10]3[CH2:14][CH2:15][CH2:16][C:9]=3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 13575338987753-08-0

Product 1

HCID 15767157HCID 15767157, compoundYield 5.1%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 8.3 g (39.1 mmol) of 2-phenyl-3,5,6,7-tetrahydro-4H-cyclopentapyrimidin-4-one in 60 mL of tetrahydrofuran was added to 1.9 g (48 mmol) of 60% sodium hydride, with external cooling. A 6.4 g (43.0 mmol) portion of 80% by weight of propargyl bromide in toluene was added to the cooled solution. The ice bath was removed and the reaction was refluxed for 6 hours. The solvent was removed in vacuo, ether was added to the residue and the reaction was washed 3 times with water and once with brine. The organic layer was dried over MgSO4 and concentrated to yield 5.0 g of crude semisolid product. The crude product was dissolved in a small amount of methylene chloride and passed through a 6 inch plug of silica gel, washing with 1 of methylene chloride. The silica gel was washed further with 1 L of ether. The ether was removed in vacuo to yield 0.5 g (5.1%) of 2-phenyl-3-propargyl-3,5,6,7-tetrahydro-4H-cyclopentapyrimidin-4-one (Compound 1) as a white solid. 1H-NMR (CDCl3) δ 2.15 (2H,m), 2.35 (1H,t), 2.95 (4H,t), 4.65 (2H,t), 7.55 (3H,m), 7.7 (2H,m).

Workup

  1. customThe ice bath was removed
  2. temperaturethe reaction was refluxed for 6 hours
  3. customThe solvent was removed in vacuo, ether
  4. additionwas added to the residue
  5. washthe reaction was washed 3 times with water
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated
  8. customto yield 5.0 g of crude semisolid product
  9. washwashing with 1 of methylene chloride
  10. washThe silica gel was washed further with 1 L of ether
  11. customThe ether was removed in vacuo

Sources & evidence

ORD record
ord-56261e9b73ac4288a04fbcf2f4b9c384
Source dataset
uspto-grants-1995_01
Patent number
US05378678

Reaction notes

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