Acetic Anhydride → 5,8-Dihydro-2-(4-formyl-1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid

HRID 867181Notes

Reaction equation

HRID 867181 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[N:8]1([C:14]2[N:15]=[CH:16][C:17]3[C:23](=[O:24])[C:22]([C:25]([OH:27])=[O:26])=[CH:21][NH:20][C:18]=3[N:19]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1>C(O)=O>[CH:1]([N:11]1[CH2:10][CH2:9][N:8]([C:14]2[N:15]=[CH:16][C:17]3[C:23](=[O:24])[C:22]([C:25]([OH:27])=[O:26])=[CH:21][NH:20][C:18]=3[N:19]=2)[CH2:13][CH2:12]1)=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12850756HCID 12850756, compound

Product 1

HCID 128507575,8-Dihydro-2-(4-formyl-1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Formic acid (140 ml) was added dropwise to acetic anhydride (200 ml) cooled on an ice bath. The solution was heated at 50° C. for 15 minutes and then cooled to 5° C. To the solution, 5,8-dihydro-2-(1-piperazinyl)-5-oxopyrido[2,3-d] pyrimidine-6-carboxylic acid (70 g) was added. The mixture was heated at 80° C. for 3 hours and then cooled. The crystals precipitated were collected by filtration and washed with ethyl ether to give 5,8-dihydro-2-(4-formyl-1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid (72.5 g). m.p. above 300° C.

Workup

  1. temperaturecooled on an ice bath
  2. temperaturecooled to 5° C
  3. temperatureThe mixture was heated at 80° C. for 3 hours
  4. temperaturecooled
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration
  7. washwashed with ethyl ether

Sources & evidence

ORD record
ord-808f374d92784998ae6d8ada0818d78e
Source dataset
uspto-grants-1978_07
Patent number
US04103011

Reaction notes

Loading…