Methyl iodide → 4-Chloro-5-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

Temperature

-78 °C

Add 4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (0.4 g; 0.0023 mol; 1.0 equiv) in THF (15 mL) and cool to −78° C. under an argon atmosphere. Add drop-wise lithium hexamethyldisilazide (4.7 mL; 0.0047 mol; 2.0 equiv; 1 M in THF). Stir the reaction at −78° C. for 30 min. Add drop-wise methyl iodide (0.29 mL; 0.0047 mol; 2.0 equiv), allow the reaction temperature to come to −20° C. slowly and stir at −20° C. for 2 h. Quench the reaction with saturated ammonium chloride aqueous and extract with EA. Evaporate the organic layer to give the title compound (0.24 g; 41.38%).

1. customthe reaction at −78° C. for 30 min
2. customto come to −20° C.
3. stirringstir at −20° C. for 2 h
4. customQuench
5. customthe reaction with saturated ammonium chloride aqueous
6. extractionextract with EA
7. customEvaporate the organic layer

ORD record

ord-e90c8c31da5343f0a55e99de79c22cdc

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148387B2