4H-Pyrido[1,2-a]pyrimidin-4-one, 3-(2-chloroethyl)-9-hydroxy-2-methyl-, hydrochloride → 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 448538Notes

Reaction equation

HRID 448538 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:8]2=[N:7][C:6]=1[CH3:17].[H][H]>[C].[Pd].C(O)(=O)C>[Cl:2][CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[CH2:12][CH2:13][CH2:14][CH:15]([OH:16])[C:8]2=[N:7][C:6]=1[CH3:17]

Participants

5

Reactant 2

HCID 250093164H-Pyrido[1,2-a]pyrimidin-4-one, 3-(2-chloroethyl)-9-hydroxy-2-methyl-, hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 155471943-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one hydrochloride (formula-5) (40 grams), acetic acid (200 ml) and palladium carbon (40 grams) was taken in an autoclave. Hydrogen gas with a pressure of 3.0-3.5 Kg/cm2 was applied to the above mixture at 35° C. for 6 hrs. The reaction was quenched with water and filtered the resultant mixture through a hyflow bed. The pH of the filtrate was adjusted to 6 using aqueous sodium hydroxide solution The reaction mixture was cooled to 0° C. and stirred for 1 hr. The solid formed was filtered, washed with water and dried to yield the title compound.

Workup

  1. customThe reaction was quenched with water
  2. filtrationfiltered the resultant mixture through a hyflow bed
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-06d1b4ce98814298ad8c33193a70363b
Source dataset
uspto-grants-2013_07
Patent number
US08481729B2

Reaction notes

Loading…