HCID 13363392, compound → HCID 13363393, compound

HRID 1980124Notes

Reaction equation

HRID 1980124 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[C:12]([N+:15]([O-])=O)[CH:13]=[CH:14][C:7]2=[N:6][C:5]=1[CH3:18].[H][H]>[Pt]=O.CO>[NH2:15][C:12]1[CH:13]=[CH:14][C:7]2[N:8]([CH:11]=1)[C:9](=[O:10])[C:4]([CH2:3][CH2:2][Cl:1])=[C:5]([CH3:18])[N:6]=2

Participants

5

Reactant 2

HCID 13363392HCID 13363392, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13363393HCID 13363393, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 40 parts of 3-(2-chloroethyl)-2-methyl-7-nitro-4H-pyrido[1,2-a]pyrimidin-4-one and 240 parts of methanol was hydrogenated at normal pressure and at room temperature with 0.5 parts of platinum oxide. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in acetonitrile and 2-propanol. The salt was filtered off and dissolved in water while heating. The solution was treated with activated charcoal. The latter was filtered off over Hyflo and the filter-cake was washed with water. The filtrate was stirred in a dilute ammonium hydroxide solution. The precipitated product was filtered off, washed with water and with petroleumether, and dried, yielding 19.4 parts of 7-amino-3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 185° C. (intermediate 9).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. filtrationThe salt was filtered off
  8. dissolutiondissolved in water
  9. temperaturewhile heating
  10. additionThe solution was treated with activated charcoal
  11. filtrationThe latter was filtered off over Hyflo
  12. washthe filter-cake was washed with water
  13. filtrationThe precipitated product was filtered off
  14. washwashed with water and with petroleumether
  15. customdried

Sources & evidence

ORD record
ord-46a9aff20aa740929a0de08905683816
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

Loading…