Ethyl 4-chloroacetoacetate → HCID 66831359, compound

HRID 405964Notes

Reaction equation

HRID 405964 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[Cl:9][CH2:10][C:11](=O)[CH2:12][C:13](OCC)=[O:14]>>[Cl:9][CH2:10][C:11]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]2[C:13](=[O:14])[CH:12]=1

Participants

3

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 66831359HCID 66831359, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 2-amino-5-fluoropyridine (5.1673 g, 46.09 mmol), ethyl 4-chloro-acetoacetate (8.097 mL, 59.92 mmol), and polyphosphoric acid (80.00 g) was stirred at 110° C. After 4 h, the mixture was removed from the heat. The cooled mixture was suspended in water (100 mL) and the mixture was neutralized with 2 N NaOH (550 mL) until the pH 7. The resulting precipitate was collected by filtration, washed with water (1 L), and air-dried overnight to give 2-(chloro-methyl)-7-fluoro-4H-pyrido[1,2-a]pyrimidin-4-one as a brown solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.94 (1 H, dd, J=4.9, 2.9 Hz), 8.14 (1 H, ddd, J=9.9, 7.1, 2.9 Hz), 7.79-7.86 (1 H, m), 6.59 (1 H, s), 4.68 (2 H, s); Mass Spectrum (ESI) m/e=212.9 (M+1).

Workup

  1. customthe mixture was removed from the heat
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water (1 L)
  4. customair-dried overnight

Sources & evidence

ORD record
ord-375dbb79ae334f5886926181fcc3c884
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

Loading…