N-bromobutanimide → 6-bromomethyl-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 586470Notes

Reaction equation

HRID 586470 reaction equation
[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([CH3:18])[C:7]2=[O:19])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:18][C:8]1[C:7](=[O:19])[N:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C:11]2[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 113119058-Cyclopentyl-6-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 111873396-bromomethyl-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-oneYield 32%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

8-Cyclopentyl-6-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (3.5 g, 12.7 mmol) and N-bromosuccinimide (2.6 g, 14.6 mmol) in carbon tetrachloride (100 ml) were irradiated with ultraviolet light allowing the temperature to reach 45° C. over 3 hours. The mixture was filtered, washed with dilute sodium sulfite solution, then brine, and dried over anhydrous magnesium sulfate. The crude product was chromatographed on silica gel eluting with 1:1 ethyl acetate:hexane to provide 6-bromomethyl-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as a crystalline solid yielding (1.46 g, 32% yield), mp 103-105° C.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with dilute sodium sulfite solution
  3. dry with materialbrine, and dried over anhydrous magnesium sulfate
  4. customThe crude product was chromatographed on silica gel eluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-cc72ea96e704486f9b5d69cd5f091208
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

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