1-(2-Hydroxyethyl)piperazine → 2-(4'-beta-Hydroxyethyl-piperazino)-5-oxo-6-carbethoxy-8-ethylpyrido(2,3-d)pyrimidine

HRID 66000Notes

Reaction equation

HRID 66000 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][N:8]([CH2:18][CH3:19])[C:6]=2[N:7]=1.[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:2]2[N:3]=[CH:4][C:5]3[C:11](=[O:12])[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][N:8]([CH2:18][CH3:19])[C:6]=3[N:7]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 122668052-Chloro-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydropyrido(2,3-d)pyrimidine

Product 1

HCID 227568342-(4'-beta-Hydroxyethyl-piperazino)-5-oxo-6-carbethoxy-8-ethylpyrido(2,3-d)pyrimidineYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.6 g. of 2-chloro-5-oxo-6-carbethoxy-8-ethyl-5,8-dihydro-pyrido(2,3-d)pyrimidine, 5.2 g. of 1-β-hydroxyethyl piperazine and 50 cm3 of toluene are heated under reflux for 2 hours. After cooling, the solution is filtered to remove the hydrochloride which has precipitated, and the organic solution is diluted with its own volume of chloroform, is washed with water and dried (MgSO4). After evaporation, the residue is recrystallised from 40 cm3 of a mixture of isopropanol (1 volume) and isopropyl ether (2 volumes). 5.14 g. (68%) of 2-(4'-β-hydroxyethyl-piperazino)-5-oxo-6-carbethoxy-8-ethylpyrido(2,3-d)pyrimidine are obtained; melting point 172° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe solution is filtered
  4. customto remove the hydrochloride which
  5. customhas precipitated
  6. additionthe organic solution is diluted with its own volume of chloroform
  7. washis washed with water
  8. dry with materialdried (MgSO4)
  9. customAfter evaporation
  10. customthe residue is recrystallised from 40 cm3 of a mixture of isopropanol (1 volume) and isopropyl ether (2 volumes)

Sources & evidence

ORD record
ord-f9a24339bd324d649a5bc310dd06507a
Source dataset
uspto-grants-1978_12
Patent number
US04129737

Reaction notes

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