Dichloromethane → HCID 57654286, compound

432 mg (2.57 mmol) of thieno[3,2-d]pyrimidine-2,4-diol was chlorinated as above (heat 100° C. overnight in 6.25 mL POCl3) to give 2,4-dichloro-thieno[3,2-d]pyrimidine after the usual workup (removal of toluene, quenching with ice and extraction with dichloromethane followed by drying over MgSO4 and concentration). Thus obtained 2,4-dichloro-thieno[3,2-d]pyrimidine was reacted without any further purification. 2,4-Dichloro-thieno[3,2-d]pyrimidine was dissolved in 25 mL ethanol and 5 mL dichloromethane and 8-oxa-3-aza-bicyclo[3.2.1]octane hydrochloride (384 mg, 2.57 mmol) and 2.1 mL triethylamine (15 mmol, 6 equivalents) were added. After stirring at room temperature for 45 minutes, the mixture was concentrated, dissolved in dichloromethane and washed with sat. NH4Cl, water and sat. NaHCO3. The organic phase was dried over MgSO4 and concentrated to give 626 mg (2.22 mmol, 86% over 2 steps) of the title compound.

1. customafter the usual workup (removal of toluene, quenching with ice and extraction with dichloromethane followed by drying over MgSO4 and concentration)
2. customThus obtained 2,4-dichloro-thieno[3,2-d]pyrimidine was reacted without any further purification
3. concentrationthe mixture was concentrated
4. dissolutiondissolved in dichloromethane
5. washwashed with sat. NH4Cl, water and sat. NaHCO3
6. dry with materialThe organic phase was dried over MgSO4
7. concentrationconcentrated

ORD record

ord-afdeefa8c8fd4abeaee7616341f0f0f6

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129371B2