Methyl iodide → HCID 86711708, compound

To a 100 mL round bottomed flask was added 4-chloro-6-methoxypteridin-7(8H)-one (2.09 g, 9.8 mmol, 1.0 equiv) and anhydrous N,N-dimethylformamide (10 mL). Anhydrous potassium carbonate (6.8 g, 49 mmol, 5 equiv) was added in one portion to the reaction flask followed by the drop wise addition of iodomethane (2.09 g, 15 mmol, 1.5 equiv) over the course of 1 minute. The reaction was then vigorously stirred at room temperature. LC/MS analysis at 14 hours indicated the reaction was complete. The reaction mixture was then passed through a glass-sintered funnel and the recovered solids were washed with N,N-dimethylformamide (1×10 mL) and dichloromethane (3×15 mL) to give a dark brown filtrate. The solvent was evaporated at reduced pressure and the resulting powder was redissolved in dichloromethane (200 mL) and washed with saturated sodium chloride solution (200 mL). The organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to yield 1.72 g (pale brown powder, 77% yield) of 4-chloro-6-methoxy-8-methylpteridin-7(8H)-one as the desired material. 1H NMR (400 MHz, DMSO-d6): δ 8.76 (s, 1H), 4.04 (s, 3H), 3.56 (s, 3H). MS (EI) for C8H7ClN4O2: 227 (MH+).

1. customThe reaction mixture was then passed through a glass-sintered funnel
2. washthe recovered solids were washed with N,N-dimethylformamide (1×10 mL) and dichloromethane (3×15 mL)
3. customto give a dark brown filtrate
4. customThe solvent was evaporated at reduced pressure
5. dissolutionthe resulting powder was redissolved in dichloromethane (200 mL)
6. washwashed with saturated sodium chloride solution (200 mL)
7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-1a684ac29423405ea2bc460dde281823

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346807B2