Ammonium Acetate → HCID 86702356, compound

HRID 1422564Notes

Reaction equation

CS([C:5]1[N:10]=[C:9](/[CH:11]=[C:12]2/[C:13](=[O:18])[NH:14][C:15](=[O:17])[S:16]/2)[CH:8]=[CH:7][N:6]=1)(=O)=O.C([O-])(=O)C.[NH4+:23]>CS(C)=O>[NH2:23][C:5]1[N:10]=[C:9](/[CH:11]=[C:12]2/[C:13](=[O:18])[NH:14][C:15](=[O:17])[S:16]/2)[CH:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(Z)-5-((2-aminopyrimidin-4-yl)methylene)thiazolidine-2,4-dione was prepared as follows. A 40 mL round bottomed vial was charged with (Z)-5-((2-(methylsulfonyl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione (203 mg, 0.712 mmol), DMSO (3 mL), ammonium acetate (543 mg, 7.04 mmol, 10 equiv.) and heated at 100° C. for 2 h. The reaction was concentrated under reduced pressure using the Genevac. The residue was partitioned between 3 mL of DCE and 3 mL of H2O and the aqueous layer was back extracted with DCE (3×3 mL). The combined organic layer was concentrated under reduced pressure to provide the desired product. (114 mg, 0.477 mmol, 67.0% yield). LC-MS m/z 223 (M+1).

Workup

concentrationThe reaction was concentrated under reduced pressure
customThe residue was partitioned between 3 mL of DCE and 3 mL of H2O
extractionthe aqueous layer was back extracted with DCE (3×3 mL)
concentrationThe combined organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-72abb139a9674346a34e6499b0810ad8
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927525B2

Reaction notes

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