2-Amino-5-bromopyridine → HCID 57494523, compound

HRID 222609Notes

Reaction equation

HRID 222609 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C([O:12]/[C:13](/[C:23](OC)=[O:24])=[C:14](/OC(=O)C)\[C:15]([O:17][CH3:18])=[O:16])(=O)C>C(O)(=O)C.CO>[CH3:18][O:17][C:15]([C:14]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]2[C:23](=[O:24])[C:13]=1[OH:12])=[O:16]

Participants

5

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 13100501HCID 13100501, compound

Product 1

HCID 57494523HCID 57494523, compoundYield 2.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

2-Amino-5-bromo-pyridine (664 mg, 3.85 mmol), dimethyl diacetoxyfumarate (1.00 g, 3.84 mmol) and glacial acetic acid (10 drops) in dry methanol (10 mL) were combined and heated to reflux. After 48 h the reaction was cooled to room temperature and concentrated in vacuo. Ethyl acetate (2 mL) was added to the residue which was sonicated for 2 min and the resulting precipitate collected by filtration and washed with cold ethyl acetate (1 mL) and dried on the pump to afford 7-bromo-3-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid methyl ester as a yellow solid (24 mg, 2%): 1H NMR (300 MHz, CDCl3) δ 4.19 (3H, s, OCH3), 7.53 (2H, d, J=1.4 Hz, H8 and H9), 9.00 (1H, d, J=1.4 Hz, H6), 10.53 (1H, br s, OH).

Workup

  1. temperatureheated to reflux
  2. concentrationconcentrated in vacuo
  3. additionEthyl acetate (2 mL) was added to the residue which
  4. customwas sonicated for 2 min
  5. filtrationthe resulting precipitate collected by filtration
  6. washwashed with cold ethyl acetate (1 mL)
  7. customdried on the pump

Sources & evidence

ORD record
ord-d8d00835ed534ee89c58d8da9658030a
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

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