Réaction #577234

Équation de réaction

Carbonic acid 2-[5-(dimethylamino-methyleneamino)-2-oxo-thiazolo [4,5-d]pyrimidin-3-yl]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester isopropyl ester

Carbonic acid 2-[5-(dimethylamino-methyleneamino)-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester isopropyl ester

HOAc

→

16

Rendement 69.0%

Carbonic acid 2-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester isopropyl ester

Rendement 69.0%

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated to a solid residue in vacuo
2. 2
   AutreThe solids were triturated with a minimum of Et2O

Mode opératoire

Carbonic acid 2-[5-(dimethylamino-methyleneamino)-2-oxo-thiazolo [4,5-d]pyrimidin-3-yl]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester isopropyl ester (15) (460 mg, 1.04 mmol) was dissolved in MeOH (5.0 mL) and HOAc (1.0 mL) was added. The reaction was warmed to 35° C. for 48 h, concentrated to a solid residue in vacuo, then subjected to flash chromatography (40-100% EtOAc-hexanes). The solids were triturated with a minimum of Et2O to yield 275 mg (69%) of 16 as a white powder: 1H NMR (400 MHz, DMSO-d6) δ 8.38 (1H, s), 6.86 (2H, bs), 5.87 (1H, d, J=5.6 Hz), 5.68 (1H, dd, J1=4.5 Hz, J2=8.3 Hz), 5.46 (1H, d, J=7.0 Hz), 4.66 (1H, septet, J=6.2 Hz), 4.58 (1H, t, J=5.8 Hz), 4.33-4.37 (1H, m), 3.96-4.03 (1H, m), 3.62-3.72 (2H, m), 1.17 (3H, d, J=6.3 Hz), 1.12 (3H, d, J=6.2 Hz); [M]+ @ m/z 386.9.

Source