Hydrochloric Acid → 2-(pyridin-4-ylamino)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride

HRID 1062320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062320
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH:17]=[C:16]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[CH:19]=4)[C:15](=[O:28])[N:14]([CH2:29][CH3:30])[C:12]=3[N:13]=2)=[CH:3][CH:2]=1.[ClH:31]>>[ClH:31].[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH:17]=[C:16]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[CH:19]=4)[C:15](=[O:28])[N:14]([CH2:29][CH3:30])[C:12]=3[N:13]=2)=[CH:3][CH:2]=1

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 99091362-(pyridin-4-ylamino)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one

Produkt 1

HCID 222201802-(pyridin-4-ylamino)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one hydrochlorideAusbeute 92 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The reaction mixture was stirred at 100° C. for a total of 60 hours, at which time RP-HPLC revealed that all dimers had been converted to 2-(pyridin-4-ylamino)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one. The reaction mixture was cooled to 45° C. and acidified by addition of 300 mL of 6N hydrochloric acid (the acidification was exothermic). The acidic solution was stirred for 4 hours at 24° C., during which time the product had precipitated as a bright yellow solid. The precipitate was filtered and washed with 200 mL of 6N hydrochloric acid, with 250 mL of water, with 800 mL of acetonitrile, and finally with 300 mL of methyl tert-butyl ether. The precipitate was dried in a vacuum oven at 40° C. for 12 hours to provide 303 g (92% yield) of 2-(pyridin-4-ylamino)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride; mp 295-300° C. (dec). Mass Spec (APCI) 439.89 m/z.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 45° C.
  2. stirringThe acidic solution was stirred for 4 hours at 24° C., during which time the product
  3. customhad precipitated as a bright yellow solid
  4. filtrationThe precipitate was filtered
  5. washwashed with 200 mL of 6N hydrochloric acid, with 250 mL of water, with 800 mL of acetonitrile
  6. customThe precipitate was dried in a vacuum oven at 40° C. for 12 hours

Quellen und Nachweise

ORD-Eintrag
ord-0f187294001148cba44a08cbe99a8573
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960662B2

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