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Diisopropylethylamine → 4-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine

HRID 1359489
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1359489
FC(F)(F)C(O)=O.[C:8]([C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1)(=[O:10])[NH2:9].Cl[C:18]1[C:19]2[C:27]([CH3:28])=[CH:26][N:25]([C:29]3[C:33]([CH:34]([CH3:36])C)=[CH:32][S:31][C:30]=3[CH3:37])[C:20]=2[N:21]=[C:22]([CH3:24])[N:23]=1.[CH:38](N(C(C)C)CC)([CH3:40])[CH3:39].C(=O)([O-])O.[Na+]>C(O)C>[C:8]([C:11]1[CH2:16][CH2:15][N:14]([C:18]2[C:19]3[C:27]([CH3:28])=[CH:26][N:25]([C:29]4[CH:33]=[CH:34][C:36]([CH:38]([CH3:40])[CH3:39])=[CH:37][C:30]=4[S:31][CH3:32])[C:20]=3[N:21]=[C:22]([CH3:24])[N:23]=2)[CH2:13][CH:12]=1)(=[O:10])[NH2:9]
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Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 224827414-Carbamoyl-1,2,3,6-tetrahydropyridine trifluoroacetateHCID 865899054-chloro-2,5-dimethyl-7-(isopropyl-2-methylthiophenyl)-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 159078794-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine
Ausbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In 4 ml of ethanol, 0.25 g of 4-carbamoyl-1,2,3,6-tetrahydropyridine trifluoroacetate and 0.35 g of 4-chloro-2,5-dimethyl-7-(isopropyl-2-methylthiophenyl)-7H-pyrrolo[2,3-d]pyrimidine were dissolved, and 0.39 g of diisopropylethylamine were added thereto. The reaction mixture was heated under reflux for 7.5 hours, and subsequently, a saturated aqueous solution of sodium hydrogencarbonate was poured into the reaction mixture. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and subsequently dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform—methanol=60:1), followed by crystallization from a mixed solvent of ethyl acetate-diethyl ether to yield 0.17 g of 4-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 7.5 hours
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialsubsequently dried over anhydrous sodium sulfate
  6. filtrationAfter the desiccant was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: chloroform—methanol=60:1)
  9. customfollowed by crystallization from a mixed solvent of ethyl acetate-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4cc1272895bf48348cd9913ea4d4aaf4
Quelldatensatz
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06600038B1

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