Propargyl bromide → 3-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

HRID 865633Notes

Reaction equation

HRID 865633 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[N:13]=[C:12]([N:16]([CH3:18])[CH3:17])[N:11]([CH3:19])[C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]#[CH:30]>CC(C)=O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH2:30][C:29]#[CH:28])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[N:13]=[C:12]([N:16]([CH3:17])[CH3:18])[N:11]([CH3:19])[C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 199752573-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

Product 1

HCID 199752633-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2.80 g (8.90 mmol) of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione in 50 mL of acetone was added 1.47 g (10.7 mmol) of potassium carbonate and 1.98 mL (17.8 mmol) of an 80% solution of propargyl bromide in toluene. It was then warmed to reflux for 2 h. It was cooled to room temperature and the mixture was filtered and washed with excess ethyl acetate. The crude product was flash chromatographed over silica gel, eluting with a 3:7 v:v mixture of ethyl acetate and hexane to give 3.1 g of the title compound as a pale yellow solid, m.p.: 61°-65° C.; 1 -NMR (CDCl3, 200 MHz) ppm 7.0 (d, 1H), 4.75 (m, 2H), 3.45 (s, 3H), 3.1 (s, 6H), 2.6 (m, 1H).

Workup

  1. temperatureIt was then warmed
  2. temperatureto reflux for 2 h
  3. filtrationthe mixture was filtered
  4. washwashed with excess ethyl acetate
  5. customchromatographed over silica gel
  6. washeluting with a 3:7 v
  7. additionv mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-1b9495fefeca49529b4ad88de367fdb4
Source dataset
uspto-grants-1996_10
Patent number
US05567670

Reaction notes

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