1-Aminoindane, (S)- → (1S,2S,4R)-4-[(6-Chloropyrimidin-4-yl)amino]-2-(hydroxymethyl)cyclopentanol

HRID 447590

Reaktionsgleichung

Reaktionsgleichung von HRID 447590
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]2[CH2:25][C@@H:12]3[O:13]C(C4C=CC(OC)=CC=4)[O:15][CH2:16][C@@H:11]3[CH2:10]2)[CH:3]=1.N[C@@H]1C2C(=CC=CC=2)CC1>>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]2[CH2:25][C@H:12]([OH:13])[C@H:11]([CH2:16][OH:15])[CH2:10]2)[CH:3]=1

Komponenten

3

Edukt 2

HCID 70000841-Aminoindane, (S)-HCID 596713556-chloro-N-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]pyrimidin-4-amine

Produkt 1

HCID 59671353(1S,2S,4R)-4-[(6-Chloropyrimidin-4-yl)amino]-2-(hydroxymethyl)cyclopentanolAusbeute 41 %

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A neat mixture of 6-chloro-N-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]pyrimidin-4-amine (120. mg, 0.332 mmol) and (S)-(+)-1-aminoindan (0.170 mL, 1.33 mmol) was heated to 180° C. for 6 h in a sealed tube using MWI. The reaction was purified via silica gel chromatography eluting with a gradient of 0 to 15% MeOH in DCM to afford the title compound (33.1 mg, 41%). LC/MS: Rt=0.90 min, ES+ 244 (AA standard).

Aufarbeitung

  1. customThe reaction was purified via silica gel chromatography
  2. washeluting with a gradient of 0 to 15% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-0e19e92d9ff044738244ac620ed18f47
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481550B2

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