Bromine → 6-bromo-8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1666245Notes

Reaction equation

HRID 1666245 reaction equation
[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([S:14][CH3:15])[N:11]=[C:12]([CH3:13])[C:7]=2[CH:6]=[CH:5][C:4]1=[O:16])[CH3:2].[Br:17]Br>C(Cl)Cl>[Br:17][C:5]1[C:4](=[O:16])[N:3]([CH2:1][CH3:2])[C:8]2[N:9]=[C:10]([S:14][CH3:15])[N:11]=[C:12]([CH3:13])[C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 576069558-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 576069666-bromo-8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (6.31 g, 26.84 mmol) in DCM was added Br2 (4.79 g, 29.52 mmol) dropwise at room temperature. Then the reaction mixture was stirred at room temperature overnight. After filtration the solid was suspended in DCM (100 mL), and triethylamine (20 mL) was added. The mixture was washed with water and dried with Na2SO4, and the product 6-bromo-8-ethyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (6.96 g, 83% yield) was obtained after evaporation of DCM. 1H NMR (400 MHz, CDCl3): δ 8.22 (s, 1H), 4.56 (q, J=7.2 Hz, 2H), 2.68 (s, 3H), 2.62 (s, 3H), 1.34 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationAfter filtration the solid
  2. additiontriethylamine (20 mL) was added
  3. washThe mixture was washed with water
  4. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-f90e2992110443d39b62254a1703bef2
Source dataset
uspto-grants-2011_10
Patent number
US08044062B2

Reaction notes

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