Dimethylformamide → HCID 21104326, compound

Temperature

70 °C

To a suspension of 4-[2-(5-chloro-2-fluoro-phenyl)-5,7-dihydro-furo[3,4-d]pyrimidin-4-ylamino]-nicotinic acid (50 mg, 0.13 mmol, 1 eq) in DMF (2 ml) was added 1-1′-carbonyldiimidazole (50 mg, 0.31 mmol, 2.4 eq) and the reaction mixture was warmed to 70° C. for 2 h. The mixture was cooled to r.t. and NH3(g) was bubbled through for 10 min. The reaction mixture was stirred at r.t. for an additional 1 h. The reaction was concentrated in vacuo and the residue was triturated with water (2×5 ml). To the crude residue was added 1 N NaOH (5 ml) and the suspension was heated to 100° C. for 2 h. The reaction mixture was cooled to room temperature and neutralized with 1 N HCl and the solid was filtered to give 4-[2-(5-Chloro-2-fluoro-phenyl)-5,7-dihydro-furo[3,4-d]pyrimidin-4-ylamino]-nicotinic amide, compound of formula (34) (25 mg, 50%) as a white solid.

1. temperatureThe mixture was cooled to r.t.
2. customNH3(g) was bubbled through for 10 min
3. concentrationThe reaction was concentrated in vacuo
4. customthe residue was triturated with water (2×5 ml)
5. additionTo the crude residue was added 1 N NaOH (5 ml)
6. temperaturethe suspension was heated to 100° C. for 2 h
7. temperatureThe reaction mixture was cooled to room temperature and neutralized with 1 N HCl
8. filtrationthe solid was filtered

ORD record

ord-dcebcb2647414455aea434791ef84dee

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977342B2