Chlorosuccinimide → 7-(2,5-dioxopyrrolidin-1-yl)-1-isobutyl-3-methyl-6-(4-(pyridin-2-yl)benzyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 1422999Notes

Reaction equation

[CH2:1]([N:5]1[C:10]2=[CH:11][N:12]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[CH:17][CH:16]=3)[CH:13]=[C:9]2[C:8](=[O:27])[N:7]([CH3:28])[C:6]1=[O:29])[CH:2]([CH3:4])[CH3:3].Cl[N:31]1[C:35](=[O:36])[CH2:34][CH2:33][C:32]1=[O:37]>C(Cl)(Cl)(Cl)Cl.CN(C=O)C>[O:37]=[C:32]1[CH2:33][CH2:34][C:35](=[O:36])[N:31]1[C:11]1[N:12]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[CH:13]=[C:9]2[C:8](=[O:27])[N:7]([CH3:28])[C:6](=[O:29])[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:10]=12

Participants

Conditions

Temperature: 100 °C

Procedure

1-isobutyl-3-methyl-6-(4-(pyridin-2-yl)benzyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (186 mg, 0.48 mmol) is dissolved in a mixture of CCl4 and DMF (3/1, v/v), and then N-chlorosuccinimide (67 mg, 0.51 mmol) is added. The reaction mixture is heated in a Biotage microwave at 100° C. for 30 min. Solvents are removed under vacuum, and the residue is purified by a semi-preparative HPLC to give pure product as white solids (40 mg, yield 20%). MS (ESI) m/z 486.2 [M+H]+.

Workup

customSolvents are removed under vacuum
customthe residue is purified by a semi-preparative HPLC

Sources & evidence

ORD record: ord-8147fc0283204a8eb54e4fe2c607b2dd
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927556B2

Reaction notes

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