Reaktion #1055411

Reaktionsgleichung

diisopropylcarbodiimide

ethoxycarbonylisothiocyanate

product

(2R)-2-[[5,6-diamino-2-[[(2-fluorophenyl)methyl]thio]-4-pyrimidinyl]amino]-1-propanol

triethylamine

→

subtitled product

[2-[[(2-fluorophenyl)methyl]thio]-6-[[(1R)-2-hydroxy-1-methylethyl]amino]-9H-purin-8-yl]-carbamic acid, Ethyl Ester

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction warmed to 70° C. for 1 hr
2. 2
   EinengenThe reaction mixture was concentrated in vacuo
3. 3
   Sonstigethe residue purified twice by silica gel chromatography
4. 4
   Wascheneluting both times with 3:1 ethyl acetate

Vorschrift

To a solution of ethoxycarbonylisothiocyanate (0.48 ml) in dry acetonitrile (20 ml) at 0° C. under an atmosphere of nitrogen was added a suspension of the product from example 4, step (e) (1.15 g) in dry acetonitrile (20 ml) containing 2.5 eq triethylamine. After stirring at 0° C. for 5 min, diisopropylcarbodiimide (0.8 ml) was added and the reaction warmed to 70° C. for 1 hr. The reaction mixture was concentrated in vacuo and the residue purified twice by silica gel chromatography, eluting both times with 3:1 ethyl acetate:DCM, to afford the subtitled product as a white solid (0.045 g).

Quelle