Methyl iodide → 7-(Benzenesulfonyl)-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

Temperature

-78 °C

To flame-dried flask under N2 was charged 0.57 ml (4.07 mmol) of diisopropylamine and 5.0 mL of dry THF. The solution was cooled to −78° C. and 1.63 mL (4.08 mmol) of a 2.5 M solution of n-butyllithium in hexanes added. The resulting mixture was brought to 0° C. and stirred for 10 minutes. After cooling the mixture again to −78° C., a solution of 1.0 g (3.40 mmol) of crude product from Method C in 10 mL of dry THF was added over a 10 minute period. The resulting mixture was stirred for 1 hour, at which time, 0.28 mL (4.50 mmol) of iodomethane were added. The reaction mixture was stirred for 2 hours, quenched with a saturated solution of NH4Cl and warmed to room temperature. The mixture was stirred for 5 minutes, diluted with water and extracted three times with ethyl acetate. The combined extracts were washed with brine, dried over MgSO4, filtered and evaporated in vacuo to obtain the title compound. LRMS: 308, 310 (M+2).

1. customTo flame-dried flask under N2
2. customwas brought to 0° C.
3. temperatureAfter cooling the mixture again to −78° C.
4. additionwere added
5. stirringThe reaction mixture was stirred for 2 hours
6. customquenched with a saturated solution of NH4Cl
7. temperaturewarmed to room temperature
8. stirringThe mixture was stirred for 5 minutes
9. additiondiluted with water
10. extractionextracted three times with ethyl acetate
11. washThe combined extracts were washed with brine
12. dry with materialdried over MgSO4
13. filtrationfiltered
14. customevaporated in vacuo

ORD record

ord-6aece2d3854349029c1866356d7ca34e

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569569B2