Ammonia → HCID 67878766, compound

HRID 256652Notes

Reaction equation

HRID 256652 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][C@H:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][CH3:29])=[O:27])[CH2:22][C@H:21]3[CH3:30])=S)=[CH:14][N:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1.[S].N>[Hg]=O.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]([NH:19][C@H:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][CH3:29])=[O:27])[CH2:22][C@H:21]3[CH3:30])=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][CH:14]=3)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5362487SulfurHCID 86745000HCID 86745000, compound

Product 1

HCID 67878766HCID 67878766, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 13 parts of methyl cis-4-[[[[4-[[(4-fluorophenyl)methyl]amino]-5-pyrimidinyl]amino]thioxomethyl]amino]-3-methyl-1-piperidinecarboxylate, 13 parts of mercury(II) oxide, 0.1 parts of sulfur and 160 parts of methanol, saturated with ammonia was stirred for 0.5 hours at reflux temperature. The reaction mixture was filtered over diatomaceous earth while hot and the filtrate was evaporated. The residue was poured into water and the product was extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was solidified in 1,1'-oxybisethane. The product was filtered off and dried, yielding 7 parts (58.5%) of methyl cis-4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-3-methyl-1-piperidinecarboxylate; mp. 152.2° C. (compound 19).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered over diatomaceous earth while hot and the filtrate
  3. customwas evaporated
  4. additionThe residue was poured into water
  5. extractionthe product was extracted with trichloromethane
  6. washThe extract was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-c3749a579a174a50b16bac9efb80f9ac
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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