HCID 66831343, compound → HCID 86663776, compound

HRID 405968Notes

Reaction equation

HRID 405968 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH2:14][OH:15]>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH:14]=[O:15]

Participants

4

Reactant 1

HCID 66831343HCID 66831343, compound

Product 1

HCID 86663776HCID 86663776, compoundYield 44.24%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-bromo-7-fluoro-2-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (5.6359 g, 20.64 mmol) and manganese(IV) oxide (17.94 g, 206.4 mmol) in toluene (137.6 mL) was heated to reflux. After 3 h, the mixture was cooled to rt and filtered through a pad of Celite™. The pad was rinsed with DCM (1 L). The filtrate was concd under reduced pressure to give 3-bromo-7-fluoro-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carbaldehyde (2.4747 g, 44.24% yield) as a bright yellow solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 10.13 (1 H, s), 9.03-9.06 (1 H, m), 8.24 (1 H, ddd, J=9.8, 7.1, 2.7 Hz), 8.00-8.05 (1 H, m); Mass Spectrum (ESI) m/e=270.9 [M+1 (79Br)] and 273.0 [M+1 (81Br)].

Workup

  1. temperaturewas heated to reflux
  2. filtrationfiltered through a pad of Celite™
  3. washThe pad was rinsed with DCM (1 L)

Sources & evidence

ORD record
ord-599179e21f4f414fae6deb5c98b226b7
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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