N-Iodosuccinimide → 8-Chloro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyrazine

HRID 449008Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[N:4]([C:8]([S:11][CH3:12])=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[I:13]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([S:11][CH3:12])=[N:9][C:10]=2[I:13])[CH:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 55 °C

Procedure

P To a solution of 8-chloro-3-methylsulfanyl-imidazo[1,5-a]pyrazine (1.75 g, 0.00876 mol) in DMF (15 mL) was added N-iodosuccinimide (3.94 g, 0.0175 mol), the resulting mixture was stirred at 55° C. for 6 hrs. The mixture was diluted with EtOAc (200 mL), washed with sat. aq. NaHCO3 (40 mL), water (2×40 mL), brine (40 mL), and dried over anhydrous sodium sulfate. The crude material was purified by silica gel chromatography to give the title compound as a yellow solid, 2.68 g, 94% yield. 1H NMR (CDCl3, 400 MHz): δ 2.72 (s, 3H), 7.36 (d, J=4.8 Hz, 1H), 7.76 (d, J=4.8 Hz, 1H).

Workup

washwashed with sat. aq. NaHCO3 (40 mL), water (2×40 mL), brine (40 mL)
dry with materialdried over anhydrous sodium sulfate
customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record: ord-87439b1cffb448068234f536f9a05e83
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481733B2

Reaction notes

Loading…