Sodium triacetoxyborohydride → 4-(5-Chloro-2-((4-(oxetan-3-yl)piperidin-1-yl)methyl)thiazolo[5,4-d]pyrimidin-7-yl)morpholine

HRID 1922762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922762
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[N:10]=[C:9]([CH:11]=O)[S:8][C:6]=2[N:7]=1.[O:19]1[CH2:22][CH:21]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[N:10]=[C:9]([CH2:11][N:26]3[CH2:27][CH2:28][CH:23]([CH:21]4[CH2:22][O:19][CH2:20]4)[CH2:24][CH2:25]3)[S:8][C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 552642454-(Oxetan-3-yl)piperidineHCID 576854055-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

Produkt 1

HCID 596057004-(5-Chloro-2-((4-(oxetan-3-yl)piperidin-1-yl)methyl)thiazolo[5,4-d]pyrimidin-7-yl)morpholineAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of 5 -chloro-7-morpholin-4-ylthiazolo [5,4-d]pyrimidine-2-carbaldehyde (1.0 g, 3.52 mmol), 4-oxetan-3-ylpiperidine (536 mg, 4.23 mmol) and molecular sieves (4 Å, powdered, 6.56 g) in DCE (30 mL) was stirred at ambient temperature for 4 h. Sodium triacetoxyborohydride (1.49 g, 7.05 mmol) was added and the mixture stirred for 6 h, then filtered through a pad of Celite® and the filtrate was concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PPC, DCM:MeOH; gradient from 100:0 to 97:3) to afford the title compound as a cream solid (334 mg, 41%). LCMS (Method A): RT=2.48 min, M+H+=410

Aufarbeitung

  1. filtrationfiltered through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resultant residue was purified by flash chromatography (Si—PPC, DCM:MeOH; gradient from 100:0 to 97:3)

Quellen und Nachweise

ORD-Eintrag
ord-e26ac85ebc0a4506b5614b76c3517a61
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

Notizen zur Reaktion

Wird geladen…