Methylamine → US10633389, Example 3-1

HRID 527467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527467
[CH3:1][C:2]1[C:3]([NH:25][C@@H:26]2[CH2:30][CH2:29][O:28][CH2:27]2)=[N:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH:22]3[CH2:24][O:23]3)[CH:15]=2)=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[CH3:31][NH2:32]>CO>[CH3:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][C:5]([C:14]2[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=2)[O:20][CH2:21][CH:22]([OH:23])[CH2:24][NH:32][CH3:31])=[N:4][C:3]=1[NH:25][C@@H:26]1[CH2:30][CH2:29][O:28][CH2:27]1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 904256505-Methyl-6-morpholino-2-(3-(oxiran-2-ylmethoxy)phenyl)-N-((R)-tetra-hydrofuran-3-yl)pyrimidin-4-amine

Produkt 1

HCID 90426219US10633389, Example 3-1Ausbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

5-Methyl-6-morpholino-2-(3-(oxiran-2-ylmethoxy)phenyl)-N—((R)-tetra-hydrofuran-3-yl)pyrimidin-4-amine (20 mg, 0.05 mmol) was dissolved in a 2N MeNH2 solution in methanol, (10 mL) and the mixture was stirred at room temperature for 14 h., concentrated under vacuum and the residue was purified by preparative HPLC to obtain the 1-(3-(5-methyl-4-morpholino-6-((R)-tetrahydrofuran-3-ylamino)pyrimidin-2-yl)phenoxy)-3-(methyl-amino)propan-2-ol (8 mg, 37% yield) as a white solid. 1H NMR (500 MHz, CD3OD) δ ppm: 8.02-7.96 (m, 2H), 7.34 (t, J=8.0 Hz, 1H), 7.05-7.00 (m, 1H), 4.85-4.80 (m, 1H), 4.20-4.14 (m, 2H), 4.07-4.01 (m, 3H), 3.93-3.84 (m, 5H), 3.78-3.74 (m, 1H), 2.96-2.92 (m, 1H), 2.88-2.82 (m, 1H), 2.53 (s, 3H), 2.42-2.35 (m, 1H), 2.11-2.04 (m, 4H); ESI-LCMS (m/z): 444.3 [M+1]+.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-799adaf154374a338becc40df315a6fa
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346802B2

Notizen zur Reaktion

Wird geladen…