Water → N-(5-(Bromomethyl)-4-(4-fluorophenyl)-6-(1-methylethyl)-2-pyrimidinyl)-N-methylmethanesulfonamide

HRID 2207004Notes

Reaction equation

HRID 2207004 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[C:12]([CH:15]([CH3:17])[CH3:16])[N:11]=[C:10]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])[N:9]=2)=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O.O>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH2:14][Br:24])=[C:12]([CH:15]([CH3:17])[CH3:16])[N:11]=[C:10]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 20771262N-[4-(4-Fluorophenyl)-5-methyl-6-(1-methylethyl)-2-pyrimidinyl]-N-methylmethanesulfonamide

Product 1

HCID 16638881N-(5-(Bromomethyl)-4-(4-fluorophenyl)-6-(1-methylethyl)-2-pyrimidinyl)-N-methylmethanesulfonamideYield 100.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(4-(4-fluorophenyl)-5-methyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (112.5 mg, 0.33 mmol, 1 equiv.) and N-bromosuccinimide (NBS) (126 mg, 0.72 mmol, 2.1 equiv.) were dissolved in 2 mL of acetonitrile. The mixture was irradiated with light of a wavelength A=310 nm for 4 hours at ambient temperature (about 20° C.). Then, water (10 mL) was added and the mixture was extracted with CH2Cl2 (3×10 mL). The combined organic phases were washed with 10 mL of brine, and the obtained solution was dried with Na2SO4. Solvent was removed under the reduced pressure to give 138.6 mg of crude N-(4-(4-fluorophenyl)-5-(bromomethyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (II), which contained 93% of N-(4-(4-fluorophenyl)-5-(bromomethyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (II) as determined by 1H-NMR integral. This product can be further purified by crystallization from MTBE/hexane mixture to afford pure material.

Workup

  1. customThe mixture was irradiated with light of a wavelength A=310 nm for 4 hours at ambient temperature (about 20° C.)
  2. extractionthe mixture was extracted with CH2Cl2 (3×10 mL)
  3. washThe combined organic phases were washed with 10 mL of brine
  4. dry with materialthe obtained solution was dried with Na2SO4
  5. customSolvent was removed under the reduced pressure

Sources & evidence

ORD record
ord-3f2cc89a4c8845f5ab1a0d1005c43a24
Source dataset
uspto-grants-2016_06
Patent number
US09376397B2

Reaction notes

Loading…