5-Bromo-2-fluoro-3-pyridinecarboxaldehyde → 6-Bromo-N-methylpyrido[2,3-d]pyrimidin-2-amine

HRID 522736Notes

Reaction equation

HRID 522736 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=O)[C:5](F)=[N:6][CH:7]=1.Cl.[CH3:12][NH:13][C:14]([NH2:16])=[NH:15]>C(#N)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[N:15]=[C:14]([NH:13][CH3:12])[N:16]=[CH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 454801925-Bromo-2-fluoro-3-pyridinecarboxaldehydeHCID 178485118HCID 178485118, compound

Product 1

HCID 588291426-Bromo-N-methylpyrido[2,3-d]pyrimidin-2-amineYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

Treat a solution of 5-bromo-2-fluoropyridine-3-carboxaldehyde (0.50 g, 2.451 mmol) and 1-methylguanidine hydrochloride (0.322 g, 2.94 mmol) in acetonitrile (20 mL) with TEA (0.947 mL, 7.35 mmol) and heat to 180° C. in the microwave for 15 min. Concentrate the mixture to dryness, treat the residue with DCM and wash with H2O, then brine. Dry the organic layer over Na2SO4, concentrate to dryness and purify via silica gel chromatography (20-100% EtOAc/Hexanes) to afford the title compound (140 mg, 24% yield). MS (m/z): 241.0 (M+1).

Workup

  1. concentrationConcentrate the mixture to dryness
  2. additiontreat the residue with DCM
  3. washwash with H2O
  4. dry with materialDry the organic layer over Na2SO4
  5. concentrationconcentrate to dryness
  6. custompurify via silica gel chromatography (20-100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-340191897e0b49d9b5800485779361fd
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

Loading…