Isopropyl chloroformate → HCID 20317724, compound

HRID 867184Notes

Reaction equation

HRID 867184 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([C:13]([OH:15])=[O:14])=[CH:9][NH:8][C:6]=2[N:7]=1.C(N(CC)CC)C.ClC(OC(C)C)=O.O[N:31]1[C:35](=[O:36])[CH2:34][CH2:33][C:32]1=[O:37]>CN(C)C=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([C:13]([O:15][N:31]3[C:35](=[O:36])[CH2:34][CH2:33][C:32]3=[O:37])=[O:14])=[CH:9][NH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 203177252-Amino-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid

Product 1

HCID 20317724HCID 20317724, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 2-amino-5,8-dihydro-5-oxopyrido[ 2,3-d]pyrimidine-6-carboxylic acid (1.70 g) and triethylamine (2.5 ml) in dried dimethylformamide (50 ml) was stirred at room temperature for 1 hour and to the suspension was added isopropyl chloroformate (1.90 ml) at 0°-5° C. The mixture was stirred at 5°-10° C. for one hour and a solution of N-hydroxysuccinimide (1.91 g) in dimethylformamide (20 ml) was added to it. The mixture was stirred at room temperature for 1.5 hours. The crystals precipitated were collected and washed with dichloromethane to give N-(2-amino-5,8-dihydro-5-oxopyrido[2,3-d]pyrimidine-6-carbonyloxy)succinimide (1.9 g) m.p. above 300° C.

Workup

  1. stirringThe mixture was stirred at 5°-10° C. for one hour
  2. stirringThe mixture was stirred at room temperature for 1.5 hours
  3. customThe crystals precipitated
  4. customwere collected
  5. washwashed with dichloromethane

Sources & evidence

ORD record
ord-a71c3a70475a466690276b3b5f98670b
Source dataset
uspto-grants-1978_07
Patent number
US04103011

Reaction notes

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