Toluene → N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide

HRID 445928Notes

Reaction equation

HRID 445928 reaction equation
Br[CH2:2][C:3]1[C:4]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[N:5][C:6]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])=[N:7][C:8]=1[CH:9]([CH3:11])[CH3:10].C1(C)C=CC=CC=1.[C:32]1([PH2:38]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:39]CC)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O>[C:32]1([P:38](=[O:39])([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:2][C:3]2[C:4]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:5][C:6]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])=[N:7][C:8]=2[CH:9]([CH3:11])[CH3:10])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 16638881N-(5-(Bromomethyl)-4-(4-fluorophenyl)-6-(1-methylethyl)-2-pyrimidinyl)-N-methylmethanesulfonamideHCID 178476774HCID 178476774, compound

Product 1

HCID 9937035N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamideYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-[5-bromomethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (10.0 g), toluene (100.0 mL), and diphenyl(ethoxy)phosphorane (6.2 g) were added to a reactor. The reaction mixture was stirred at 90˜100° C. for 9 hours and then water (80.0 mL) was added thereto. The separated organic layer was concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1:1) to obtain diphenyl[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-ylmethyl]phosphine oxide as a white solid (9.4 g, yield 73%).

Workup

  1. concentrationThe separated organic layer was concentrated under reduced pressure
  2. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1:1)

Sources & evidence

ORD record
ord-e2efe2fb18aa4261a8541aa777fdfe16
Source dataset
uspto-grants-2013_07
Patent number
US08476432B2

Reaction notes

Loading…