Benzoyl Peroxide → HCID 22648121, compound

HRID 394093Notes

Reaction equation

HRID 394093 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[N:5]=[C:4]([S:17][CH3:18])[N:3]=1.[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([S:17][CH3:18])=[N:5][C:6]=1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22648011HCID 22648011, compound

Product 1

HCID 22648121HCID 22648121, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 5.4 g of 4-chloro-6-(2,4-difluorophenyl)-5-methyl-2-(methylthio)pyrimidine. 3.69 g of N-bromosuccinimide, and 460 mg of benzoyl peroxide in 75 mL of CCl4 was heated to reflux and stirred at this temperature for 6 h, then cooled in the freezer for 1 h. The solids were filtered and washed liberally with cold CCl4, and the filtrate was concentrated. The residue was purified by flash chromatography on a Biotage 40M column, eluting with a gradient system of 99:1 to 97:3 hexanes-acetone to yield the title compound. Mass spectrum (ESI) 367 (M+1).

Workup

  1. temperatureto reflux
  2. temperaturecooled in the freezer for 1 h
  3. filtrationThe solids were filtered
  4. washwashed liberally with cold CCl4
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography on a Biotage 40M column
  7. washeluting with a gradient system of 99:1 to 97:3 hexanes-acetone

Sources & evidence

ORD record
ord-31a0fabcabc74fc48652363a2afc6799
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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