Dichloromethane → 4-[4-(4-Fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1-{4-[(4-hydroxybenzyl)oxy]benzyl}-1,3,5-triazin-2(1H)-one

HRID 1477730Notes

Reaction equation

HRID 1477730 reaction equation
ClCCl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][N:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)[C:19](=[O:32])[N:18]=3)[CH2:13][CH:12]=2)=[CH:7][CH:6]=1.B(Br)(Br)Br>O>[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][N:20]([CH2:23][C:24]4[CH:25]=[CH:26][C:27]([O:30][CH2:31][C:24]5[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=5)=[CH:28][CH:29]=4)[C:19](=[O:32])[N:18]=3)[CH2:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 1178396084-[4-(4-Fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1-(4-methoxybenzyl)-1,3,5-triazin-2(1H)-one

Product 1

HCID 1178396504-[4-(4-Fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1-{4-[(4-hydroxybenzyl)oxy]benzyl}-1,3,5-triazin-2(1H)-oneYield 28.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dichloromethane solution (8.0 mL) of 4-[4-(4-fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1-(4-methoxybenzyl)-1,3,5-triazin-2(1H)-one (200 mg, 0.510 mmol) synthesized in Reference Synthesis Example 352, boron tribromide (1.53 mL, 1.53 mmol) was added at 0° C. and the resultant mixture was stirred at room temperature for 1 day. After the completion of the reaction, to the reaction solution, water was added and extraction with chloroform from the reaction solution was performed. The organic layer was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (chloroform/ethyl acetate→methanol/ethyl acetate) to obtain the title compound (35.0 mg, yield: 18%) of Synthesis Example 483a and the title compound (7.15 mg, yield: 3%) of Synthesis Example 483b.

Workup

  1. additionwas added at 0° C.
  2. customAfter the completion of the reaction
  3. extractionextraction with chloroform from the reaction solution
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography (chloroform/ethyl acetate→methanol/ethyl acetate)
  6. customto obtain

Sources & evidence

ORD record
ord-24c43c0f2a32446c92324f8a24328b29
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

Loading…