Hydrochloric Acid → 8-(2-Chloroethyl)-5,8-dihydro-2-(1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid hydrochloride

HRID 1658137Notes

Reaction equation

HRID 1658137 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[CH:12][C:13]3[C:19](=[O:20])[C:18]([C:21]([O:23]CC)=[O:22])=[CH:17][N:16]([CH2:26][CH2:27][Cl:28])[C:14]=3[N:15]=2)[CH2:6][CH2:5]1)(=O)C.Cl>>[ClH:28].[Cl:28][CH2:27][CH2:26][N:16]1[C:14]2[N:15]=[C:10]([N:7]3[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]3)[N:11]=[CH:12][C:13]=2[C:19](=[O:20])[C:18]([C:21]([OH:23])=[O:22])=[CH:17]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 13334740Ethyl 2-(4-acetyl-1-piperazinyl)-8-(2-chloroethyl)-5,8-dihydro-5-oxopyrido[2,3-d]-pyrimidine-6-carboxylate

Product 1

HCID 681486698-(2-Chloroethyl)-5,8-dihydro-2-(1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid hydrochlorideYield 196.2%

Procedure

A mixture containing 1.0 g of ethyl 2-(4-acetyl-1-piperazinyl)-8-(2-chloroethyl)-5,8-dihydro-5-oxopyrido[2,3-d]-pyrimidine-6-carboxylate and 12 ml of 20% aqueous hydrochloric acid was heated on a steam bath for 2 hours, during which period crystals separated out. The crystals were collected, after cooling, and recrystallized from diluted aqueous ethanol containing a small amount of concentrated hydrochloric acid to yield 0.9 g of the product, m.p. 280°C with decomposition.

Workup

  1. temperaturewas heated on a steam bath for 2 hours, during which period crystals
  2. customseparated out
  3. customThe crystals were collected
  4. temperatureafter cooling
  5. customrecrystallized from diluted aqueous ethanol containing a small amount of concentrated hydrochloric acid

Sources & evidence

ORD record
ord-d2d201fdb79e469cab4b309c7379e1ac
Source dataset
uspto-grants-1976_06
Patent number
US03962443

Reaction notes

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