Iodine → HCID 178462348, compound

4-Hydroxy-2,5,6-triaminopyrimidine 2HCl (18.0 g, 0.084 mol) was suspended in a mixed solution (540 ml) of methanol and water (3:2), to which was added dropwise mercaptoethyl alcohol (1.0 ml) and then a solution of the crude phenylhydrazone (18.9 g) as previously prepared in a mixed solution (200 ml) of methanol and water (3:2) was poured into the suspension. The mixture was stirred in an argon atmosphere at room temperature for 1 hour and then stirred under heat at 60°-70° C. for 40 minutes. The reaction solution was cooled to -10° C. and into the solution was poured over a period of 10 minutes a solution of iodine (40 g, 0.158 mol), potassium iodide (66 g, 0.398 mol), potassium ferricyanide (40 g, 0.122 mol) and 80% formic acid (40 ml) in water (1 lit.). After air was bubbled into the solution at 0° C. for 1.5 hours, the reaction solution as concentrated in vacuo, the residue was extracted with 10% ammonia water (1 lit.), insoluble matter was filtered off, the filtrate was concentrated, the residue was again dissolved in 2% ammonia water (2 lit.) and separated by ion-exchange resin column chromatography (DOWEX 1×8; 10 cm×40 cm; 0.15 N ammonium formate buffer solution (pH 9)). The effluent was concentrated in vacuo, the residue was dissolved in 10% ammonia water (240 ml) and decolorized by activated charcoal. The solution was concentrated in vacuo to 1/3 of the total amount, left to stand overnight under ice-cooling, the precipitated pale yellow solid was washed with ice water and ethanol and dried in vacuo (80° C., 6 hrs.) to give 5.00 g (0.021 mole) of l-biopterin.

1. additionwas poured into the suspension
2. stirringstirred
3. temperatureunder heat at 60°-70° C. for 40 minutes
4. temperatureThe reaction solution was cooled to -10° C. and into the solution
5. customAfter air was bubbled into the solution at 0° C. for 1.5 hours
6. concentrationthe reaction solution as concentrated in vacuo
7. extractionthe residue was extracted with 10% ammonia water (1 lit.), insoluble matter
8. filtrationwas filtered off
9. concentrationthe filtrate was concentrated
10. dissolutionthe residue was again dissolved in 2% ammonia water (2 lit.)
11. customseparated by ion-exchange resin column chromatography (DOWEX 1×8; 10 cm×40 cm; 0.15 N ammonium formate buffer solution (pH 9))
12. concentrationThe effluent was concentrated in vacuo
13. dissolutionthe residue was dissolved in 10% ammonia water (240 ml)
14. concentrationThe solution was concentrated in vacuo to 1/3 of the total amount
15. waitleft
16. waitto stand overnight under ice-
17. temperaturecooling
18. washthe precipitated pale yellow solid was washed with ice water and ethanol
19. customdried in vacuo (80° C., 6 hrs.)

ORD record

ord-d57a409610944898b927e92088c218cc

Source dataset

uspto-grants-1991_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05043446