Methyl iodide → 2,4-Dichloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidine

温度

-78 °C

1.4 g 5-bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (4) (5.2 mmol) was dissolved in 200 mL of THF. After cooling to −78° C., 9.75 mL of BuLi (1.6M solution in Hexanes, 15.6 mmol) was slowly added over a period of 30 minutes, then stirred for 30 minutes at −78° C. before 396 uL of MeI (6.24 mmol) was dropwise added into the reaction mixture over a period of one hour. The reaction mixture was stirred at −78° C. for one more hour and quenched by adding 20 mL of saturated aqueous NH4Cl solution at this temperature. The reaction mixture was then partitioned between 100 mL of saturated NaHCO3 and 100 mL of EtOAc. The organic layer was separated and the aqueous layer is extracted with EtOAc (3×100 mL). Combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the crude title compound which was used without further purification.

1. additionwas dropwise added into the reaction mixture over a period of one hour
2. customquenched
3. additionby adding 20 mL of saturated aqueous NH4Cl solution at this temperature
4. customThe reaction mixture was then partitioned between 100 mL of saturated NaHCO3 and 100 mL of EtOAc
5. customThe organic layer was separated
6. extractionthe aqueous layer is extracted with EtOAc (3×100 mL)
7. washCombined organic layers were washed with brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated

ORDレコード

ord-b9697b694f8447869d50c6062860e566

出典データセット

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08592432B2