Ammonia → (5-aminopyridin-3-yl)(7-tert-butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

HRID 82151Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:18]3[CH:17]=[N:16][CH:15]=[N:14][C:13]=3[N:12]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1.[NH3:23]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[NH2:23][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:18]3[CH:17]=[N:16][CH:15]=[N:14][C:13]=3[N:12]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Copper sulfate pentahydrate (55 mg, 0.24 mmol) was added to (5-bromopyridin-3-yl)(7-tert-butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone (292 mg, 0.81 mmol) (see Preparation 30) and concentrated ammonia solution (20 mL). The mixture was heated in a sealed vessel at 140° C. for 17 hours. The reaction mixture was evaporated in vacuo and the residue was stirred in aqueous hydrochloric acid (10 mL, 2M) at room temperature for 17 hours. The reaction mixture was basified to pH 9 using saturated aqueous sodium carbonate then extracted with DCM (3×20 mL). The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo to afford the title compound as a white solid in 49% yield, 240 mg.

Workup

customThe reaction mixture was evaporated in vacuo
extractionthen extracted with DCM (3×20 mL)
dry with materialThe combined organic extracts were dried over magnesium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-dd4a7124c8dd49e49e889376485d2330
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846698B2

Reaction notes

Loading…