Acetic Acid → PD-166326

HRID 3211

Reaktionsgleichung

Reaktionsgleichung von HRID 3211
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14](S(C)(=O)=O)[N:15]=[CH:16][C:11]=2[CH:10]=1.[OH:25][CH2:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30].C(O)(=O)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14]([NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[C:27]([CH2:26][OH:25])[CH:28]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 802933-Aminobenzyl alcoholHCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Produkt 1

HCID 447700PD-166326

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 0.155 g (0.40 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.500 g (4.10 mmol) of 3-(hydroxymethyl)aniline was heated in a 180° C. oil bath for 10 minutes. At ca. 120° C., 2 mL of glacial acetic acid were added to dissolve the gum. Water (20 mL) was added to precipitate a solid. The mixture was filtered. The cake was washed well with water and dried; wt 0.130 g. Purification was effected by silica gel chromatography eluting with chloroform and then with ethyl acetate to obtain the fraction containing the pure product. The ethyl acetate eluent was concentrated to 1 mL volume. The crystals that separated one inducement were filtered and washed with 0.5 mL of ethyl acetate and then 1 mL of ether; wt 0.059 g; mp 215°-217° C.

Aufarbeitung

  1. dissolutionto dissolve the gum
  2. customto precipitate a solid
  3. filtrationThe mixture was filtered
  4. washThe cake was washed well with water
  5. customdried
  6. customPurification
  7. washeluting with chloroform
  8. customwith ethyl acetate to obtain the fraction
  9. additioncontaining the pure product
  10. concentrationThe ethyl acetate eluent was concentrated to 1 mL volume
  11. customThe crystals that separated one inducement
  12. filtrationwere filtered
  13. washwashed with 0.5 mL of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4b3709d670944052a53ca165365f8b96
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733914

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