Ammonia → HCID 19785352, compound

HRID 256650Notes

Reaction equation

HRID 256650 reaction equation
[C:1]1([CH2:7][NH:8][C:9]2[C:14]([NH:15][C:16]([NH:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]3)=S)=[CH:13][N:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N>[Hg]=O.CO>[C:1]1([CH2:7][N:8]2[C:16]([NH:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]3)=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][CH:13]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 19785231HCID 19785231, compound

Product 1

HCID 19785352HCID 19785352, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 24 parts of ethyl 4-[[[[4-[(phenylmethyl)amino]-5-pyrimidinyl]amino]thioxomethyl]amino]-1-piperidinecarboxylate, 24 parts of mercury(II) oxide and 240 parts of methanol, saturated with ammonia was stirred overnight at reflux temperature. The reaction mixture was filtered while hot and the filtrate was evaporated. The residue was taken up in a mixture of trichloromethane and ethanol. After washing with water, the organic layer was evaporated and the residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 20.3 parts (92.1%) of ethyl 4-[[9-(phenylmethyl)-9H-purin-8-yl]amino]-1-piperidinecarboxylate; mp. 156.9° C. (compound 9).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered while hot and the filtrate
  3. customwas evaporated
  4. additionThe residue was taken up in a mixture of trichloromethane and ethanol
  5. washAfter washing with water
  6. customthe organic layer was evaporated
  7. customthe residue was crystallized from acetonitrile
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-b23f6d53725f4127a8b7f9f77a7a9bc6
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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