Dimethylformamide → 4-(Methylthio)thieno[2,3-d]pyrimidine-6-carbaldehyde

Temperature

-78 °C

4-(Methylthio)thieno[2,3-d]pyrimidine (J. Heterocycl. Chem. 1975, 12, 921-924) (1 g) in THF (5 mL) was added to a preformed solution of LDA [BuLi (1.6M in hexanes, 3.8 mL) and di-isopropylamine (0.85 mL)] in THF (20 mL) at −78° C. The reaction mixture was allowed to stir for 1 hour at −78° C. and then DMF (1.1 mL) was added. The reaction mixture was stirred at −78° C. for 30 minutes then allowed to warm to ambient temperature and stirred for a further 3 hours. The reaction mixture was diluted with water and the product was extracted with EtOAc (4×30 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with DCM afforded the title compound as a white solid (1.17 g, 51%);

1. stirringThe reaction mixture was stirred at −78° C. for 30 minutes
2. temperatureto warm to ambient temperature
3. stirringstirred for a further 3 hours
4. extractionthe product was extracted with EtOAc (4×30 mL)
5. washThe combined organic extracts were washed with brine (30 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification by flash chromatography on silica eluting with DCM

ORD record

ord-8a63ec814d604338be6716c269bb00d0

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07476677B2