Phosphorus oxychloride → 6-chloro-9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-9H-purine

HRID 2248800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2248800
Cl.[C:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16](O)=O)[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:21]=1[NH2:35].P(Cl)(Cl)(Cl)=O>>[Cl:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]2[C:21]=1[N:35]=[C:16]([CH2:15][CH:12]1[CH2:13][CH2:14][N:9]([CH2:8][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:10][CH2:11]1)[N:26]2[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1

Komponenten

4

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 140128442-(1-Benzylpiperidin-4-yl)acetic acid hydrochlorideHCID 140224096-chloro-N4-(4-fluorobenzyl)pyrimidine-4,5-diamine

Produkt 1

HCID 197852696-chloro-9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-9H-purineAusbeute 75 %

Versuchsvorschrift

A mixture of 20.65 parts of 1-(phenylmethyl)-4-piperidineacetic acid hydrochloride, 19.5 parts of 6-chloro-N4 -[(4-fluorophenyl)methyl]-4,5-pyrimidinediamine and 510 parts of phosphoryl chloride was stirred and refluxed for 13 hours. The reaction mixture was evaporated. The residue was poured into ice water. The whole was treated with sodium hydroxide. The product was extracted with 4-methyl-2-pentanone. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (97:3 by volume) as eluent. The first fraction was collected and the eluent was evaporated, yielding 23.6 parts (75%) of 6-chloro-9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]-methyl]-9H-purine as an oily residue (compound 1).

Aufarbeitung

  1. temperaturerefluxed for 13 hours
  2. customThe reaction mixture was evaporated
  3. additionThe residue was poured into ice water
  4. additionThe whole was treated with sodium hydroxide
  5. extractionThe product was extracted with 4-methyl-2-pentanone
  6. washThe extract was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol
  12. customThe first fraction was collected
  13. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-cab5d04b479d47b697d0792842657677
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05041448

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