Propargyl bromide → HCID 19048543, compound

HRID 1779896Notes

Reaction equation

HRID 1779896 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][C:11](=[O:13])[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][C:21](C)([O-])[CH3:22].[K+].C(Br)C#C>CN(C=O)C.C1(C)C=CC=CC=1.CCOCC>[C:1]1([C:7]2[N:12]([CH2:22][C:21]#[CH:20])[C:11](=[O:13])[CH2:10][CH:9]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 7842Propargyl bromideHCID 23665647Potassium tert-butoxideHCID 178515557HCID 178515557, compound

Product 1

HCID 19048543HCID 19048543, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3.95 g (15.8 mmol) of 5,6-dihydro-2,6-diphenylpyrimidin-4-one in 15 mL of DMF was added 2.07 g (18.5 mmol) of solid potassium t-butoxide. The mixture was stirred for 10 rain and 2.60 g (17.5 mmol) of an 80% by weight solution of propargyl bromide in toluene was added. The mixture was stirred at room temperature for 4 days, diluted with 175 mL of ether, washed with four 50 mL portions of water and dried over MgSO4. Removal of the solvent on the rotovap left 2.47 g of crude product which was purified by flash chromatography on silica gel eluted with an ether-hexane gradient to afford 0.72 g of 5,6-dihydro-2,6-diphenyl-3-propargylpyrimidin-4-one (Compound 15) as an oil.

Workup

  1. additionwas added
  2. washwashed with four 50 mL portions of water
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent on the rotovap
  5. waitleft 2.47 g of crude product which
  6. customwas purified by flash chromatography on silica gel
  7. washeluted with an ether-hexane gradient

Sources & evidence

ORD record
ord-4bd335eb884f4caebfb15c0a78edd739
Source dataset
uspto-grants-1997_05
Patent number
US05629264

Reaction notes

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