Hydrochloric Acid → 5-Amino-3H-thiazolo[4,5]pyrimidine-2-one

Temperatur

25 °C

To a solution of NaOH (0.6 g, 15 mmol, 3 eq) in water (20 ml) was added 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-thione (0.92 g, 5 mmol, 1.0 eq). The mixture was stirred to dissolve. An aqueous solution of H2O2 (0.68 g, 2.3 ml (30%), 20 mmol, 4 eq) was slowly added dropwise to the above solution, keeping the temperature below 50° C. The reaction was then cooled down to room temperature (about 25° C.). Concentrated HCl (37%, 6 ml) was added to the above solution until the pH is less than 1. The mixture is stirred at room temperature for 30 minutes. Celite (2 g) was added to the suspension and the suspension was filtered and washed with water (10 ml). To the filtrate was added 50% NaOH solution to adjust the pH to 5-5.5, stirred for 30 minutes, filtered, washed with water, and dried at 50° C. under vacuum to give 0.52 g (62%) of 5-amino-3H-thiazolo[4,5-d]pyrimidin-2-one as a pale yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 6.70 (s, 2H, ex. D2O), 8.2 (s, 1H), 12.2 (br s, 1H, ex. D2O); MS (+)-ES [M+H]+ m/z 169.

1. dissolutionto dissolve
2. customthe temperature below 50° C
3. stirringThe mixture is stirred at room temperature for 30 minutes
4. additionCelite (2 g) was added to the suspension
5. filtrationthe suspension was filtered
6. washwashed with water (10 ml)
7. additionTo the filtrate was added 50% NaOH solution
8. stirringstirred for 30 minutes
9. filtrationfiltered
10. washwashed with water
11. customdried at 50° C. under vacuum

ORD-Eintrag

ord-e541e7201e9a46e9b372d44cb2b31a37

Quelldatensatz

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07781581B2