Ammonia → HCID 19785352, compound

HRID 2248803Notes

Reaction equation

HRID 2248803 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-97cc647595e5402985b2704b4fb500fc
Source dataset
uspto-grants-1991_08
Patent number
US05041448

Reaction notes

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