Tetrahydrofuran → 1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

HRID 1766171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766171
[CH3:1][N:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:11]3[C:15]4=[N:16][CH:17]=[CH:18][CH:19]=[C:14]4[C:13]([C:20]([O:22]C)=[O:21])=[CH:12]3)[C:5]=2[CH:4]=[CH:3]1.O1CCCC1.[Li]>O>[CH3:1][N:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:11]3[C:15]4=[N:16][CH:17]=[CH:18][CH:19]=[C:14]4[C:13]([C:20]([OH:22])=[O:21])=[CH:12]3)[C:5]=2[CH:4]=[CH:3]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 3028194LithiumHCID 21110083methyl 1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Produkt 1

HCID 211100531-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acidAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To 1.2 g (3.7 mmol) of methyl 1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate were successively added 13.5 cm3 of tetrahydrofuran, 0.47 g (11.2 mmol) of lithium hydroxyde, monohydrate and 13.5 cm3 of distilled water. The reaction mixture was heated at reflux temperature for 4 hours and then concentrated to dryness in vacuo (2.7 kPa). The residue was dissolved into 72 cm3 of distilled water and the mixture was extracted with 35 cm3 of ethyl acetate. The aqueous phase was cooled to about 5° C. and 10 cm3 of 1N hydrochloric acid were added dropwise (pH ca. 3). The resulting precipitate was filtered, washed twice with 20 cm3 of distilled water and dried in vacuo at about 50° C. to yield 0.93 g of 1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid as off-white crystals. mp>260° C.; IR spectrum (KBr): 3461; 3152; 2951; 2571; 1678; 1590; 1544; 1452; 1263; 1204; 916; 808; 774; 746; 681 and 607 cm−1.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 4 hours
  3. concentrationconcentrated to dryness in vacuo (2.7 kPa)
  4. dissolutionThe residue was dissolved into 72 cm3 of distilled water
  5. extractionthe mixture was extracted with 35 cm3 of ethyl acetate
  6. addition10 cm3 of 1N hydrochloric acid were added dropwise (pH ca. 3)
  7. filtrationThe resulting precipitate was filtered
  8. washwashed twice with 20 cm3 of distilled water
  9. customdried in vacuo at about 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-166943f1166143639b7b0c7a07c676e5
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230007B2

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