Isopropyl chloroformate → N-[5,8-dihydro-2-(4-formyl-1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carbonyloxy]succinimide

HRID 867182Notes

Reaction equation

HRID 867182 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:10]=[CH:11][C:12]3[C:18](=[O:19])[C:17]([C:20]([OH:22])=[O:21])=[CH:16][NH:15][C:13]=3[N:14]=2)[CH2:5][CH2:4]1)=[O:2].C(N(CC)CC)C.ClC(OC(C)C)=O.O[N:38]1[C:42](=[O:43])[CH2:41][CH2:40][C:39]1=[O:44]>ClCCl.CN(C)C=O>[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:10]=[CH:11][C:12]3[C:18](=[O:19])[C:17]([C:20]([O:22][N:38]4[C:42](=[O:43])[CH2:41][CH2:40][C:39]4=[O:44])=[O:21])=[CH:16][NH:15][C:13]=3[N:14]=2)[CH2:5][CH2:4]1)=[O:2]

Participants

7

Reactant 4

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 128507575,8-Dihydro-2-(4-formyl-1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid

Product 1

HCID 12866372N-[5,8-dihydro-2-(4-formyl-1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carbonyloxy]succinimideYield 90.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5,8-dihydro-2-(4-formyl-1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid (273 g) and triethylamine (299 ml) in dried dichloromethane (3500 ml) was stirred well at room temperature for one hour. To the suspension, isopropyl chloroformate (221 g) was added dropwise with cooling at 0°-10° C. and the reaction mixture was stirred for 2 hours. A solution of N-hydroxysuccinimide (207 g) in dimethylformamide (350 ml) was added to the mixture and the resulting mixture was kept at 5°-10° C. for additional 2 hours. The crystalline product was collected by filtration and washed successively with water (2000 ml) and acetone (2000 ml) to give N-[5,8-dihydro-2-(4-formyl-1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carbonyloxy] succinimide (326 g). m.p. above 300° C.

Workup

  1. temperaturewith cooling at 0°-10° C.
  2. stirringthe reaction mixture was stirred for 2 hours
  3. waitthe resulting mixture was kept at 5°-10° C. for additional 2 hours
  4. filtrationThe crystalline product was collected by filtration
  5. washwashed successively with water (2000 ml) and acetone (2000 ml)

Sources & evidence

ORD record
ord-d76ea2ae5e8e4b36aa4ffde92fd9b171
Source dataset
uspto-grants-1978_07
Patent number
US04103011

Reaction notes

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