Hydrochloric Acid → HCID 66831343, compound

HRID 405967Notes

Reaction equation

HRID 405967 reaction equation
C([O:4][CH2:5][C:6]1[N:7]=[C:8]2[CH:17]=[CH:16][C:15]([F:18])=[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]=[C:15]([F:18])[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 66831396HCID 66831396, compound

Product 1

HCID 66831343HCID 66831343, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A heterogeneous mixture of (3-bromo-7-fluoro-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)methyl acetate (7.7539 g, 24.61 mmol), HCl (6.972 mL, 83.67 mmol), and 1,4-dioxane (70.31 mL) was heated under stirring at 70° C. After 4 h, the mixture was cooled to rt and the mixture was concd under reduced pressure. The residue was diluted with water (100 mL) and treated with 28% ammonium hydroxide (10 mL) until pH neutral. The precipitate was filtered, washed with water (300 mL), and dried under high vacuum overnight to give 3-bromo-7-fluoro-2-(hydroxyl-methyl)-4H-pyrido[1,2-a]pyrimidin-4-one as a brown solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.97 (1 H, ddd, J=4.9, 2.8, 0.7 Hz), 8.17 (1 H, ddd, J=9.8, 7.1, 2.8 Hz), 7.88 (1 H, ddd, J=9.8, 5.4, 0.7 Hz), 5.35 (1 H, br. s.), 4.60 (2 H, s); Mass Spectrum (ESI) m/e=273.0 [M+1 (79Br)] and 274.9 [M+1 (81Br)].

Workup

  1. temperaturewas heated
  2. temperaturethe mixture was cooled to rt
  3. filtrationThe precipitate was filtered
  4. washwashed with water (300 mL)
  5. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-784568b7899849328ca71a5ff3ebc89f
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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