Acetic Acid → 3-bromo-2-(chloromethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 405953Notes

Reaction equation

HRID 405953 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:6]2[C:7](=[O:9])[CH:8]=1.[Br:15]N1C(=O)CCC1=O.C(O)(=O)C.O>C(Cl)Cl>[Br:15][C:8]1[C:7](=[O:9])[N:6]2[C:10]([CH3:14])=[CH:11][CH:12]=[CH:13][C:5]2=[N:4][C:3]=1[CH2:2][Cl:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 67184N-bromobutanimideHCID 7763672-(chloromethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 668313843-bromo-2-(chloromethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(chloromethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (3.5648 g, 17.09 mmol), N-bromosuccinimide (3.35 g, 18.79 mmol), and acetic acid (48.2 mL, 843 mmol) was stirred at rt. After 4.5 h, the mixture was poured into water (200 mL) and the resulting precipitate was collected by filtration, washed with water (200 mL), and dried to give an orange solid. The orange solid was dissolved in DCM (100 mL), dried over Na2SO4, filtered, and concd under reduced pressure to give 3-bromo-2-(chloromethyl)-6-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.76 (1 H, dd, J=9.0, 7.0 Hz), 7.47-7.52 (1 H, m), 7.04-7.09 (1 H, m), 4.71 (2 H, s), 2.95 (3 H, s); Mass Spectrum (ESI) m/e=288.9 (M+1).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water (200 mL)
  3. customdried
  4. customto give an orange solid
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-3f6a191a5f0a46e396b73db23f929d0c
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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