HCID 15037327, compound → HCID 15037370, compound

HRID 1460523Notes

Reaction equation

HRID 1460523 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[C:15]([NH:16][C:17]([NH:19][CH:20]3[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:22][CH2:21]3)=S)=[CH:14][N:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1>[Hg]=O.C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]([NH:19][CH:20]3[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:22][CH2:21]3)=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][CH:14]=3)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 15037327HCID 15037327, compound

Product 1

HCID 15037370HCID 15037370, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 74 parts of ethyl 4-[[[[4-[[(4-fluorophenyl)methyl]amino]-5-pyrimidinyl]amino]thioxomethyl]amino]hexahydro-1H-azepine-1-carboxylate, 39 parts of mercury(II) oxide and 240 parts of ethanol was stirred for 1 hour at reflux temperature. The reaction mixture was filtered while hot over diatomaceous earth and the filtrate was evaporated. The residue was taken up in water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of 1,1'-oxybisethane and acetonitrile. The product was filtered off and dried, yielding 29 parts (46.8%) of ethyl 4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]hexahydro-1H-azepine-1-carboxylate; mp. 156.7° C. (compound 17).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered while hot over diatomaceous earth
  3. customthe filtrate was evaporated
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from a mixture of 1,1'-oxybisethane and acetonitrile
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-4379c41a0d064d6c821165a13d7c025d
Source dataset
uspto-grants-1991_12
Patent number
US05071846

Reaction notes

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