Benzyl mercaptan → 4-(Benzylsulfanyl)-7h-pyrrolo[2,3-d]pyrimidine

Temperatur

85 °C

To a round bottomed flask with a stir bar was added 4-chloro-1H-pyrrolo-[2,3-d]pyrimidine (5.07 g, 33.0 mmol), 1.00 M of KO-t-Bu in THF (49.5 mL, 49.5 mmol), and benzenemethanethiol (5.81 mL, 49.5 mmol) in isopropyl alcohol (350 mL). The reaction mixture was heated to reflux at 85° C. under an atmosphere of nitrogen. After 48 h, the reaction mixture was cooled and solvent was removed in vacuo. To the residue was added water (300 mL) and the solution was filtered to collect the resulting white solid. The solid was washed with diethyl ether and MeOH and dried under vacuum to afford the product as a white solid (6.29 g, 79% yield). LC/MS: Rt=1.68 min, ES+ 242 (FA standard). Reference: Pathak, A. K., Pathak, V., Seitz, L. E., Suling, W. J., Reynolds, R. C. J. Med. Chem., 2004, 47, 273-276.

1. temperatureThe reaction mixture was heated
2. temperaturethe reaction mixture was cooled
3. customsolvent was removed in vacuo
4. additionTo the residue was added water (300 mL)
5. filtrationthe solution was filtered
6. customto collect the resulting white solid
7. washThe solid was washed with diethyl ether and MeOH
8. customdried under vacuum

ORD-Eintrag

ord-66ba66f2e393456ca40a45eedadbc85a

Quelldatensatz

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08207177B2