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Ethanol → HCID 19785347, compound

HRID 2248804
Notes
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Reaction equation

HRID 2248804 reaction equation
[CH:1]1([NH:4][C:5]2[C:10]([NH:11][C:12]([NH:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]3)=S)=[CH:9][N:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1.C(O)C>[Hg]=O.CN(C)C(=O)C>[CH:1]1([N:4]2[C:12]([NH:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]3)=[N:11][C:10]3[C:5]2=[N:6][CH:7]=[N:8][CH:9]=3)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 702EthanolHCID 19785282HCID 19785282, compound

Product 1

HCID 19785347HCID 19785347, compoundYield 14.1%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 15.7 parts of ethyl 4-[[[[4-(cyclopropylamino)-5-pyrimidinyl]amino]thioxomethyl]amino]-1-piperidinecarboxylate, 20 parts of mercury(II) oxide, 40 parts of ethanol and 135 parts of N,N-dimethylacetamide was stirred overnight at 80° C. The reaction mixture was filtered over diatomaceous earth while hot. The filtrate was poured into water and the product was extracted with dichloromethane. The organic layer was dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 2.2 parts (14.1%) of ethyl 4-[(9-cyclopropyl-9H-purin-8-yl)amino]-1-piperidinecarboxylate; mp. 177.0° C. (compound 17).

Workup

  1. filtrationThe reaction mixture was filtered over diatomaceous earth while hot
  2. additionThe filtrate was poured into water
  3. extractionthe product was extracted with dichloromethane
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from acetonitrile
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-4d7d019a24bd449799d5156f83ca9c02
Source dataset
uspto-grants-1991_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05041448

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes