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

To a solution of 20 (shown in the scheme 4) (200 mg, 1.18 mmol) in THF (11 mL) was added n-BuLi (566 μL, 1.42 mmol, 2.5M in THF) very slowly at −78° C. and the mixture was stirred for 15 min at the same conditions. A solutions of dimethyl disulfide (160 uL, 1.77 mmol) and MeI (110 μL, 1.77 mmol) in THF (1 mL) was added drop wise. The reaction mixture was stirred for 2 h at −78° C., quenched with saturated aqueous NH4Cl solution, and extracted with DCM. The extract was dried over anhydrous Na2SO4 and concentrated to afford the title compound 280 (210 mg, 82% yield) as a yellowish solid. MS (m/z): 217.0 (M+H) (found).

1. stirringThe reaction mixture was stirred for 2 h at −78° C.
2. customquenched with saturated aqueous NH4Cl solution
3. extractionextracted with DCM
4. dry with materialThe extract was dried over anhydrous Na2SO4
5. concentrationconcentrated

ORD record

ord-44e475dd0b8f4918b5f487b35012d7f3

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790729B2