Ethyl bromoacetate → HCID 178473167, compound

HRID 1906762Notes

Reaction equation

[C:1]1([N:7]2[C:16]([OH:17])=[C:10]3[N:11]=[CH:12][N:13]=[C:14]([SH:15])[C:9]3=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])O.[K+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(O)C>[C:1]1([N:7]2[C:16]([OH:17])=[C:10]3[N:11]=[CH:12][N:13]=[C:14]([S:15][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:9]3=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1.22 g of 2-phenyl-3-hydroxy-7-mercapto-pyrazolo [4,3-d]pyrimidine was suspended in 100 ml of ethanol, and 0.5 g of potassium hydrogen carbonate was added. While heating the mixture at 80° C., 1 g of ethyl bromoacetate was dropwise added, and the heating and reaction were continued for further 2 hours. Then, the solvent was distilled off. Water was added to the residue, and the residue was dissolved. The solution was acidified with hydrochloric acid, and the precipitated crystals were extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The remaining solid was recrystallized from acetone-chloroform.

Workup

customthe heating and reaction
distillationThen, the solvent was distilled off
additionWater was added to the residue
dissolutionthe residue was dissolved
extractionthe precipitated crystals were extracted with chloroform
dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off
customThe remaining solid was recrystallized from acetone-chloroform

Sources & evidence

ORD record: ord-6199a50db54b450b94e7c80312065807
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04654348

Reaction notes

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