Hydrochloric Acid → HCID 66831374, compound

HRID 405984Notes

Reaction equation

HRID 405984 reaction equation
C([O:4][CH2:5][C:6]1[N:7]=[C:8]2[CH:17]=[CH:16][CH:15]=[CH:14][N:9]2[C:10](=[O:13])[C:11]=1[Br:12])(=O)C.Cl.O1CCOCC1.[OH-].[NH4+]>O>[Br:12][C:11]1[C:10](=[O:13])[N:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]2=[N:7][C:6]=1[CH2:5][OH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 312751,4-DioxaneHCID 66831360HCID 66831360, compound

Product 1

HCID 66831374HCID 66831374, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A heterogeneous mixture of the (3-bromo-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)methyl acetate (4.24 g, 1.0 equiv.), conc. HCl (8.0 equiv.) and 1,4-dioxane (39 mL) was heated with stirring at 70° C. for 3 h. LCMS showed the completion of reaction. The residue was diluted with water (100 mL) and treated with 28% ammonium hydroxide (10 mL) to pH 10. The precipitate was filtered, washed with water (200 mL) and dried under high vacuum to give 3-bromo-2-(hydroxylmethyl)-4H-pyrido[1,2-a]pyrimidin-4-one as tan solid. Used without further purification: 1HNMR (400 MHz, DMSO-d6): δ 8.96-8.98 (dd, 1H), 8.03-8.08 (m,1H), 7.74-7.76 (dd, 1H), 7.43-7.48 (m,1H), 5.3 (t,1H), 4.6 (d,2H).

Workup

  1. temperaturewas heated
  2. customthe completion of reaction
  3. filtrationThe precipitate was filtered
  4. washwashed with water (200 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-88c5b9ef727b469693f78822c51e9400
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

Loading…