Ethyl 4-[[[[4-[(2-furanylmethyl)amino]-5-pyrimidinyl]amino]thioxomethyl]-amino]-1-piperidinecarboxylate → ethyl 4-[[9-(2-furanylmethyl)-9H-purin-8-yl]amino]-1-piperidinecarboxylate

HRID 256649Notes

Reaction equation

HRID 256649 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[C:13]([NH:14][C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]2)=S)=[CH:12][N:11]=[CH:10][N:9]=1>[Hg]=O.C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]2)=[N:14][C:13]2[C:8]1=[N:9][CH:10]=[N:11][CH:12]=2

Participants

4

Reactant 1

HCID 19785223Ethyl 4-[[[[4-[(2-furanylmethyl)amino]-5-pyrimidinyl]amino]thioxomethyl]-amino]-1-piperidinecarboxylate

Product 1

HCID 19785341ethyl 4-[[9-(2-furanylmethyl)-9H-purin-8-yl]amino]-1-piperidinecarboxylateYield 21.5%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4 parts of ethyl 4-[[[[4-[(2-furanylmethyl)amino]-5-pyrimidinyl]amino]thioxomethyl]-amino]-1-piperidinecarboxylate, 6 parts of mercury(II)oxide and 80 parts of ethanol was stirred for 2 hours at reflux temperature. The whole was filtered while hot over Hyflo® and the filtrate was evaporated. The residue was crystallized from a mixture of acetonitrile and ethanol. The product was filtered off and dried, yielding 0.8 parts (21.5%) of ethyl 4-[[9-(2-furanylmethyl)-9H-purin-8-yl]amino]-1-piperidinecarboxylate; mp. 171.9° C. (compound 7).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe whole was filtered while hot over Hyflo®
  3. customthe filtrate was evaporated
  4. customThe residue was crystallized from a mixture of acetonitrile and ethanol
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-4e51488da485456c8ba79e6fcfc9b6e1
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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