N-Iodosuccinimide → 3-(8-Chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)-1-(hydroxymethyl)cyclobutanol

HRID 1163223Notes

Reaction equation

[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]2[N:12]([C:16]([CH:19]3[CH2:22][C:21]([CH2:24][OH:25])([OH:23])[CH2:20]3)=[N:17][CH:18]=2)[CH:13]=[CH:14][N:15]=1>CN(C)C=O>[Cl:9][C:10]1[C:11]2[N:12]([C:16]([CH:19]3[CH2:20][C:21]([CH2:24][OH:25])([OH:23])[CH2:22]3)=[N:17][C:18]=2[I:1])[CH:13]=[CH:14][N:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Under inert atmosphere N-iodosuccinimide (3.6 g, 0.016 mol) and 3-(8-chloro-imidazo[1,5-a]pyrazin-3-yl)-1-hydroxymethyl-cyclobutanol (3.16 g, 0.012 mol) were dissolved in N,N-dimethylformamide (30 mL) and heated at 60° C. for 3.0 hours. The reaction mixture was then concentrated in vacuo to a dark oil and purified by HPFC Jones 20 g silica gel column, eluting with 5% MeOH: CH2Cl2 to yield a light brown fluffy solid which was triturated with diethyl ether and hexanes to afford the title compound; MS (ES+): m/z 379.85 (100) [MH+], 381.80 (30) [MH+++]; HPLC: tR=2.30 min (OpenLynx, polar—5 min).

Workup

concentrationThe reaction mixture was then concentrated in vacuo to a dark oil
custompurified by HPFC Jones 20 g silica gel column
washeluting with 5% MeOH
customCH2Cl2 to yield a light brown fluffy solid which
customwas triturated with diethyl ether and hexanes

Sources & evidence

ORD record: ord-5e93f70c0755419a9740150bfd63cc66
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820662B2

Reaction notes

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