Triethylamine → (S)-4-Amino-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile

HRID 75288

Reaktionsgleichung

Reaktionsgleichung von HRID 75288
[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([C@@H:17]([NH2:19])[CH3:18])=[C:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:9]=2)[CH:4]=[CH:3]1.Cl[C:21]1[C:26]([C:27]#[N:28])=[C:25](Cl)[N:24]=[C:23]([S:30][CH3:31])[N:22]=1.CC[N:34](CC)CC>C1COCC1.CCOC(C)=O>[NH2:34][C:21]1[C:26]([C:27]#[N:28])=[C:25]([NH:19][C@H:17]([C:7]2[N:6]=[C:5]3[CH:4]=[CH:3][N:2]([CH3:1])[C:10]3=[CH:9][C:8]=2[N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH3:18])[N:24]=[C:23]([S:30][CH3:31])[N:22]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 42016204,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 86707976(S)-1-(1-Methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

Produkt 1

HCID 86707979(S)-4-Amino-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrileAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S)-1-(1-Methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (200 mg, 0.768 mmol) was dissolved in THF (5 mL) along with 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (169 mg, 0.768 mmol) and Et3N (0.118 mL, 0.845 mmol) to give an orange suspension. The reaction mixture was stirred at room temperature for 2 h, then diluted with EtOAc and washed aq 1M HCl (3×15 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was then loaded onto an ISCO® silica gel cartridge (12 g) and eluted using an EtOAc/Hexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a white solid (117 mg, 61%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36-1.50 (m, 3 H), 2.43-2.47 (m, 3 H), 2.72-2.88 (m, 2 H), 2.99-3.15 (m, 2 H), 3.68-3.89 (m, 7 H), 5.89-6.02 (m, 1 H), 6.46-6.58 (m, 1 H), 7.04-7.18 (m, 1 H), 7.21-7.42 (m, 2 H), 7.53-7.65 (m, 1 H), 7.82-7.95 (m, 1 H); ESI-MS m/z [M+H]+ calc'd for C20H24N8OS, 425.5; found 425.5.

Aufarbeitung

  1. customto give an orange suspension
  2. washwashed aq 1M HCl (3×15 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washeluted
  7. customThe product was collected
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8f1cf9110a8a47e7b739f8c32b634ae3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835420B2

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