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

HRID 1395043Notes

Reaction equation

HRID 1395043 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 an 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 an 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-20166e1f4e7b48adb3ba62bf0b1173a4
Source dataset
uspto-grants-1980_05
Patent number
US04201781

Reaction notes

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