Hydrochloric Acid → 4H-Pyrido[1,2-a]pyrimidin-4-one, 3-(2-chloroethyl)-9-hydroxy-2-methyl-, hydrochloride

HRID 448543Notes

Reaction equation

HRID 448543 reaction equation
C([O:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.P(Cl)(Cl)([Cl:18])=[O:17].[ClH:21].[C:22]1([CH3:28])[CH:27]=[CH:26]C=[CH:24][CH:23]=1>>[ClH:18].[Cl:21][CH2:24][CH2:23][C:22]1[C:28](=[O:17])[N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[C:10]2=[N:15][C:27]=1[CH3:26]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 24813Phosphorus oxychlorideHCID 903342-Amino-3-benzyloxypyridine

Product 1

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

Conditions

Temperature
50 °C

Procedure

A mixture of 3-benzyloxy-2-aminopyridine (formula-2) (100 grams), toluene (3.5 L) and phosphorusoxychloride (139 ml) was heated to 50° C. 3-acetyldihydrofuran-2(3H)-2-one (218 grams) (formula-3) was added to the reaction mixture, heated to 95° C. and stirred for 18 hrs. The solvent was distilled off under reduced pressure to obtain a residue which was cooled to 40° C. and toluene (500 ml) was added to it. A solution of concentrated hydrochloric acid (600 ml) was added to the reaction mixture, heated to 60° C. and stirred for 6 hrs. The reaction mixture was cooled to 0° C. A solid crystallized out which was filtered, washed with toluene and dried at 50° C. to yield the title compound.

Workup

  1. temperatureheated to 95° C.
  2. distillationThe solvent was distilled off under reduced pressure
  3. customto obtain a residue which
  4. temperaturewas cooled to 40° C.
  5. temperatureheated to 60° C.
  6. stirringstirred for 6 hrs
  7. temperatureThe reaction mixture was cooled to 0° C
  8. customA solid crystallized out which
  9. filtrationwas filtered
  10. washwashed with toluene
  11. customdried at 50° C.

Sources & evidence

ORD record
ord-3c99cdcfa14b48278ebcce844b25983e
Source dataset
uspto-grants-2013_07
Patent number
US08481729B2

Reaction notes

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