6-ethyl-5-methoxy-2-phenyl-3-propargyl-4(3H)-pyrimidinone → HCID 19690665, compound

HRID 1462Notes

Reaction equation

HRID 1462 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]([CH2:15][C:16]#[CH:17])[C:5](=[O:18])[C:4]=1[O:19]C)[CH3:2]>O>[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]([CH2:15][C:16]#[CH:17])[C:5](=[O:18])[C:4]=1[OH:19])[CH3:2]

Participants

3

Reactant 1

HCID 196907076-ethyl-5-methoxy-2-phenyl-3-propargyl-4(3H)-pyrimidinone2×

Product 1

HCID 19690665HCID 19690665, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an oven dried 3-neck round bottom flask, equipped with a magnetic stirrer, a thermometer, an addition funnel, a septum and a nitrogen inlet, was added 10 mL of 1M boron tribromide in methylene chloride, by syringe. The BBr3 was cooled to -65 C with a dry ice/acetone bath and 0.9 g (3.3 mmol) of 6-ethyl-5-methoxy-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 183) was added dropwise through an addition funnel. The reaction stirred at low temperature for 1.5 h. The reaction progress was checked by G.C. and was complete at this time. Water was slowly added and the reaction was left to stir for 1 h at room temperature. The reaction mixture was transferred to an addition funnel and extracted three times with methylene chloride. The organic layers were combined and dried over MgSO4, then concentrated to yield 0.6 g (72% yield) of 6-ethyl-5-hydroxy-2-phenyl-3-propargyl-4(3H)-pyrimidinone, as a white solid. M.p. 152°-154° C. 1H-NMR (CDCl3) 1.25(3H,t), 2.4(1H,t), 2.7(2H,q), 4.65(2H,d), 6.25(1H,s), 7.55(3H,m), 7.65(2H,m).

Workup

  1. customTo an oven dried 3-neck round bottom flask
  2. customequipped with a magnetic stirrer
  3. additiona thermometer, an addition funnel, a septum and a nitrogen inlet, was added 10 mL of 1M boron tribromide in methylene chloride
  4. temperatureThe BBr3 was cooled to -65 C with a dry ice/acetone bath
  5. waitthe reaction was left
  6. stirringto stir for 1 h at room temperature
  7. customThe reaction mixture was transferred to an addition funnel
  8. extractionextracted three times with methylene chloride
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-504c94f80cd14c1f86ab5786e3c9e054
Source dataset
uspto-grants-1998_03
Patent number
US05726124

Reaction notes

Loading…