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

HRID 222154Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.O(C(C)(C)C)[K].C1COCC1.[C:22]1([CH2:28][SH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(C)C>[CH2:28]([S:29][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 85 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-66ba66f2e393456ca40a45eedadbc85a
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207177B2

Reaction notes

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