Lithium diisopropylamide → 4-Chloro-6-(methylthio)thieno[3,2-d]pyrimidine

Temperature

-78 °C

To a suspension of compound 6.2 (5 mmol) in dry THF (25 mL) was added LDA (6 mmol, 2.0 M in heptane/THF/ethylbenzene) at −78° C. under an atmosphere of N2. After stirring at −78° C. for 30 minutes, the mixture was transferred to a pre-cooled solution of methyl methanethiosulfonate (8 mmol) in of dry THF (10 mL) at −78° C. The resulting mixture was slowly warmed to room temperature and stirred for 2 hours. The reaction was quenched by the addition of several portions of sat. aq. NH4Cl, concentrated and partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was separated, dried and concentrated to give a residue that was purified by flash column chromatography on silica gel to give 4-chloro-6-methylsulfanyl-thieno[3,2-d]pyrimidine (compound 63.1).

1. temperatureThe resulting mixture was slowly warmed to room temperature
2. stirringstirred for 2 hours
3. customThe reaction was quenched by the addition of several portions of sat. aq. NH4Cl
4. concentrationconcentrated
5. custompartitioned between EtOAc and saturated aqueous NaHCO3
6. customThe organic layer was separated
7. customdried
8. concentrationconcentrated
9. customto give a residue that
10. customwas purified by flash column chromatography on silica gel

ORD record

ord-118d52125df141b78a514890a0dc7820

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601725B2