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

HRID 405982Notes

Reaction equation

HRID 405982 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]2[CH:13]=[CH:12][CH:11]=[CH:10][N:6]2[C:7](=[O:9])[CH:8]=1.[Br:14]NC(=O)CCC(N)=O.C(O)(=O)C.O>C(Cl)Cl>[Br:14][C:8]1[C:7](=[O:9])[N:6]2[CH:10]=[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 51550272-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 9834204N-Bromosuccinamide

Product 1

HCID 132329173-Bromo-2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (3.564 g, 1.0 equiv.), N-bromosuccinamide (1.0 equiv.) and acetic acid (48.2 mL) was stirred at rt for 4.5 h, at this point LCMS showed reaction was complete. 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 solid was dissolved in DCM (100 mL), dried over Na2SO4, filtered and cond under reduced pressure to give desired 3-bromo-2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one as an orange solid which was carried forward without any further purification: 1HNMR (400 MHz, DMSO-d6): δ 8.94-8.97 (dd,1H), 8.03-8.08 (m,1H), 7.76-7.80 (dd, 1H), 7.43-7.48 (m,1H), 4.7 (s,2H).

Workup

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

Sources & evidence

ORD record
ord-a41268510b534359b0361d86c7d25cbf
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

Loading…