Ammonia → HCID 178492154, Verbindung

HRID 1621375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1621375
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16]3[N:24]=[CH:23][N:22]=[C:21]4[C:17]=3[N:18]=[CH:19][N:20]4C3CCCCO3)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.Cl.N>>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16]3[N:24]=[CH:23][N:22]=[C:21]4[C:17]=3[N:18]=[CH:19][NH:20]4)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1

Komponenten

4

Edukt 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 66600240HCID 66600240, Verbindung

Produkt 1

HCID 178492154HCID 178492154, VerbindungAusbeute 80,1 %

Versuchsvorschrift

A solution of 6-methoxy-N-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)pyridin-3-amine (190 mg, 471 μmol) in 2N aqueous HCl (2.0 mL, 4 mmol) was heated briefly at 100° C. in an oil bath, and then the heater was turned off and the mixture allowed to slowly cool and stand overnight. An essentially clean conversion was observed. The solution was neutralized with aqueous ammonia, and the precipitated product was collected by filtration washing with a small volume of water and dried under vacuum. N-(6-Methoxypyridin-3-yl)-3-(9H-purin-6-yl)pyridin-2-amine (120.4 mg, 80.1% yield) was obtained as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ 13.80 (br. s., 1H); 12.33 (br. s., 1H); 9.73 (br. s., 1H); 9.10 (s, 1H); 8.70 (s, 1H); 8.50-8.58 (m, 1H); 8.25-8.34 (m, 1H); 8.08-8.20 (m, 1H); 6.95-7.07 (m, 1H); 6.79-6.90 (m, 1H); 3.85 (s, 3H). m/z (ESI, +ve) 320.0 (M+H)+.

Aufarbeitung

  1. temperatureto slowly cool
  2. filtrationthe precipitated product was collected by filtration
  3. washwashing with a small volume of water
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dfa12376dd4b4b9c8b271085005f45ad
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

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