Water → 2-(1-Aminoethyl)-3-bromo-7-fluoro-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1715036Notes

Reaction equation

HRID 1715036 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[CH:14]([NH:16]C(=O)OCC1C=CC=CC=1)[CH3:15].B(Br)(Br)Br.O.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:16][CH:14]([C:3]1[N:4]=[C:5]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][N:6]2[C:7](=[O:8])[C:2]=1[Br:1])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 58796910Benzyl 1-(3-bromo-7-fluoro-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)ethylcarbamate

Product 1

HCID 587968532-(1-Aminoethyl)-3-bromo-7-fluoro-4H-pyrido[1,2-a]pyrimidin-4-oneYield 104.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

E2 (312 mg, 0.74 mmol) was dissolved in 18 mL of anhydrous dichloromethane. BBr3 (3.7 mL, 1M in dichloromethane) was added dropwise at −10° C. under nitrogen. Stirring was continued at −10° C. for 50 min., then at room temperature for 45 min. Water was added to quench the reaction. The dichloromethane layer was set aside. The aqueous layer was adjusted to pH 8 with sodium bicarbonate and extracted with 30% isopropanol in chloroform 4 times. The dichloromethane layer was washed with brine and the brine layer was adjusted to pH 8 with sodium bicarbonate and extracted with 30% isopropanol in chloroform 1 times. The combined 30% isopropanol in chloroform extracts were dried and concentrated to give 222 mg of E3 as a solid, which was used directly for next step.

Workup

  1. waitat room temperature for 45 min
  2. customto quench
  3. customthe reaction
  4. extractionextracted with 30% isopropanol in chloroform 4 times
  5. washThe dichloromethane layer was washed with brine
  6. extractionextracted with 30% isopropanol in chloroform 1 times
  7. dry with materialThe combined 30% isopropanol in chloroform extracts were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5a38fd7d5a9a4428bde5e077ea122cff
Source dataset
uspto-grants-2010_09
Patent number
US07799795B2

Reaction notes

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