5-Amino-2-methoxyphenol → HCID 58928321, Verbindung

HRID 851911

Reaktionsgleichung

Reaktionsgleichung von HRID 851911
[Br:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9](Cl)[C:4]=2[CH:3]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[NH2:16].C(N(C(C)C)CC)(C)C>C(O)CCC>[Br:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:16][C:15]3[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:13]([OH:12])[CH:14]=3)[C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 743145-Amino-2-methoxyphenolHCID 81531DiisopropylethylamineHCID 457898276-Bromo-4-chloro-7H-pyrrolo[2,3-D]pyrimidine

Produkt 1

HCID 58928321HCID 58928321, VerbindungAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (100 mg, 0.41 mmol), prepared as in reference 1, is mixed with 3-hydroxy-4-methoxyaniline (170 mg, 1.22 mmol) and diisopropylethylamine (213 μL, 1.22 mmol) in n-butanol (1.3 mL). The mixture is heated to 120° C. for 18 hours, with stirring. The reaction is then cooled to ambient temperature and the solvent is removed. The resultant crude product is purified by flash column chromatography using a gradient of 3-5% MeOH in DCM to yield 5-(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2-methoxy-phenol (96 mg; 66%); 1H NMR (500 MHz, d-methanol) δ 8.17 (s, 1H), 7.16 (s, 1H), 6.98 (d, J=8.6 Hz, 1H), 6.92 (d, J=8.6 Hz, 1H), 6.61 (s, 1H), 3.87 (s, 3H), 3.75 (s, 3H); LC-ESMS observed [M+H]+ 349.0 (calculated for C14H13BrN4O2, 348.0).

Aufarbeitung

  1. temperatureThe reaction is then cooled to ambient temperature
  2. customthe solvent is removed
  3. customThe resultant crude product is purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7e93572a87fb41efb1bbf94b4966e397
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253166B2

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