Dimethylformamide → HCID 11414935, compound

Temperature

125 °C

To a solution of ethyl 5-bromo-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidine-carboxylate (i.e. the product of Step B) (1.07 g, 3.7 mmol) in N,N-dimethylformamide (15 mL) was added thionyl chloride (0.54 mL, 7.5 mmol). The reaction mixture was stirred for 2 h. The solvent was removed with a rotary evaporator. The residue was dissolved in dichloromethane, washed with saturated aqueous sodium bicarbonate and dried (Na2SO4). The solvent was removed with a rotary evaporator. The residue was dissolved in tetrahydrofuran (2 mL), and a methanolic solution of ammonia (7 N, 2 mL) was added. The reaction mixture was placed in a sealed vial and heated in a microwave reactor at 125° C. for 2 h. The reaction mixture was allowed to stand over the weekend. Dichloromethane was added and the reaction mixture was filtered. The solvent was removed with a rotary evaporator. The residue was purified by MPLC (10→30% ethyl acetate in hexanes as eluant) to afford the title product, a compound of the present invention, as a white solid (0.52 g).

1. customThe solvent was removed with a rotary evaporator
2. dissolutionThe residue was dissolved in dichloromethane
3. washwashed with saturated aqueous sodium bicarbonate
4. dry with materialdried (Na2SO4)
5. customThe solvent was removed with a rotary evaporator
6. dissolutionThe residue was dissolved in tetrahydrofuran (2 mL)
7. additiona methanolic solution of ammonia (7 N, 2 mL) was added
8. additionDichloromethane was added
9. filtrationthe reaction mixture was filtered
10. customThe solvent was removed with a rotary evaporator
11. customThe residue was purified by MPLC (10→30% ethyl acetate in hexanes as eluant)

ORD record

ord-276461d7b59b4086901eeba606bad3bf

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863220B2