2-Aminopyridine → 2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1075292Notes

Reaction equation

HRID 1075292 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Cl:8][CH2:9][C:10](=O)[CH2:11][C:12](OCC)=[O:13]>>[Cl:8][CH2:9][C:10]1[N:7]=[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]2[C:12](=[O:13])[CH:11]=1

Participants

3

Reactant 2

HCID 104392-AminopyridineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 51550272-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one

Procedure

37.7 g 2-pyridinamine was dissolved in about 250 g polyphosphoric acid, at 40°-50°, using a mechanically driven stirrer. To this mixture was added, dropwise, 54 ml ethyl 4-chloroacetoacetate. After the addition, the mixture was heated to about 125° for 1/2 hour. After cooling to about 50°, the mixture was poured into 1500 ml of ice water, and the mixture was extracted with an equal volume of chloroform. After drying and evaporation of chloroform, about 45 g 2-(chloromethyl)-4H-pyrido[1,2-a] pyrimidin-4-one (m.p. 171°-174°) was obtained.

Workup

  1. additionTo this mixture was added
  2. additionAfter the addition
  3. temperaturethe mixture was heated to about 125° for 1/2 hour
  4. temperatureAfter cooling to about 50°
  5. extractionthe mixture was extracted with an equal volume of chloroform
  6. customAfter drying
  7. customevaporation of chloroform

Sources & evidence

ORD record
ord-51d8c9f0269e46278fcd44d7fff2a781
Source dataset
uspto-grants-1983_07
Patent number
US04395551

Reaction notes

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