Benzyl Alcohol → 6-(Phenylmethoxy)-9H-purin-2-amine

HRID 458295

Reaktionsgleichung

[H-].[Na+].N#N.[CH2:5]([OH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:14]1[N:22]=[C:21]([NH2:23])[N:20]=[C:19]2[C:15]=1[NH:16][CH:17]=[N:18]2>C1(C)C=CC=CC=1>[CH2:5]([O:12][C:14]1[N:22]=[C:21]([NH2:23])[N:20]=[C:19]2[C:15]=1[NH:16][CH:17]=[N:18]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 115 °C

Versuchsvorschrift

60% Sodium hydride in mineral oil (2.36 g, 0.059 moles) was charged to a 500 mL 3-neck flask equipped with magnetic stirring, temperature probe, condenser, and N2 inlet. Toluene (250 mL) was added. Benzyl alcohol (50 mL) was added dropwise over 30 minutes. After addition of benzyl alcohol, the reaction was stirred 10 minutes. Then 6-chloro-2-aminopurine (5.00 g, 0.029 moles) was added and the reaction mixture was heated to reflux (115° C.) for 4.5 hours. The reaction mixture was filtered hot through a coarse glass fritted funnel and 11.65 g of wet off-white solids were obtained. The wet solids were triturated with CH2Cl2 (100 mL) and water (100 mL). After 10 minutes of stirring the solids had dissolved. The aqueous layer was separated and the pH was lowered to 9 over 3 minutes with 6 M HCl. A white solid precipitate formed. The slurry was filtered, washed with water (50 mL), and dried (in vacuo at 50° C.) to a constant weight to provide the desired product as off-white crystals (5.15 g).

Aufarbeitung

temperaturethe reaction mixture was heated
filtrationThe reaction mixture was filtered hot through a coarse glass fritted funnel

Quellen und Nachweise

ORD-Eintrag: ord-b128acacab3c4a0381b11082d87f1ad6
Quelldatensatz: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07189849B2

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