Triethylamine → 6-bromo-1H,2H,4H-pyrido(2,3-d)(1,3)oxazin-2-one

HRID 445725Notes

Reaction equation

HRID 445725 reaction equation
Br.[NH2:2][C:3]1[C:8]([CH2:9][OH:10])=[CH:7][C:6]([Br:11])=[CH:5][N:4]=1.C(N(CC)CC)C.Cl[C:20](OC(Cl)(Cl)Cl)=[O:21]>ClCCl>[Br:11][C:6]1[CH:5]=[N:4][C:3]2[NH:2][C:20](=[O:21])[O:10][CH2:9][C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 441196112-Amino-5-bromo-3-(hydroxymethyl)pyridine hydrobromide

Product 1

HCID 159259906-bromo-1H,2H,4H-pyrido(2,3-d)(1,3)oxazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A mixture of 2-amino-5-bromo-3-hydroxymethylpyridine hydrobromide (Apollo, Cheshire, UK, 0.528 mmol) in dichloromethane (1.25 ml) and triethylamine (1.162 mmol) was cooled with an ice-bath. Was added to the RM trichloromethyl chloroformate (0.317 mmol) in dichloromethane and the RM was stirred for 30 min at 0° C. and 1 h at rt. The RM was diluted with dichloromethane, washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and separated by flash chromatography (heptane/EtOAc 0% to 80%). The fractions containing product were evaporated together to give the title compound as a yellow solid. (HPLC: tR 2.16 min (Method A); M+H=229, 231 MS-ES)

Workup

  1. temperaturewas cooled with an ice-bath
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was absorbed on silica gel
  7. customseparated by flash chromatography (heptane/EtOAc 0% to 80%)
  8. additionThe fractions containing product
  9. customwere evaporated together

Sources & evidence

ORD record
ord-9ee95319140d42a7bd6d5471c7ff8b3d
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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