1,2-Dichloroethane → Ethyl 2-(4-acetyl-1-piperazinyl)-8-(2-chloroethyl)-5,8-dihydro-5-oxopyrido[2,3-d]-pyrimidine-6-carboxylate

HRID 1658130Notes

Reaction equation

HRID 1658130 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[CH:12][C:13]3[C:19]([O:20]CC)=[C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:17]=[N:16][C:14]=3[N:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:28][CH2:29][CH2:30]Cl>>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:11]=[CH:12][C:13]3[C:19](=[O:20])[C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][N:16]([CH2:30][CH2:29][Cl:28])[C:14]=3[N:15]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 111,2-DichloroethaneHCID 21532580Ethyl 2-(4-acetyl-1-piperazinyl)-5-ethoxypyrido[2,3-d]pyrimidine-6-carboxylate

Product 1

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

Procedure

A solution of 1.0 g of ethyl 2-(4-acetyl-1-piperazinyl)-5-ethoxypyrido[2,3-d]pyrimidine-6-carboxylate in 10 ml of 1,2-dichloroethane was heated to reflux for 15 hours. After removal of an excess of the reagent by distillation, the resulting solid was taken up in chloroform and the chloroform solution washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off to leave a solid which was recrystallized from ethyl acetate to give 0.65 g of the product, m.p. 205° - 206°C.

Workup

  1. temperatureto reflux for 15 hours
  2. customAfter removal of an excess of the reagent
  3. distillationby distillation
  4. washthe chloroform solution washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customto leave a solid which
  8. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ebac1a57b69148f284740b707792ea87
Source dataset
uspto-grants-1976_06
Patent number
US03962443

Reaction notes

Loading…