N,N-Dimethylaniline → 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine

Temperature

0 °C

The 1H-Pyrazolo[3,4-d]pyrimidin-4-ol (5.00 g, 36.73 mmol) was dissolved in 68.5 mL of phosphorous oxychloride and 9.31 mL of N,N-dimethyl aniline (73.47 mmol). This mixture was heated to reflux (120 C) for 90 minutes to completion affording a dark red solution. The mixture was concentrated in vacuo and cooled to 0° C. in an ice bath. The residue was poured into ice water and stirred for three minutes. The acidic melt was extracted with ether, and the organics were combined. The organic was washed with cold water, cold half saturated NaHCO3 solution, brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford the 4-chloro-1H-pyrazolo[3,4-d]pyrimidine as a light yellow powder (2.30 g, 41%). 1H NMR (DMSO-d6, 400 MHz) δ 8.84 (s, 1H), 8.46 (s, 1H), NH not observed.

1. temperatureThis mixture was heated
2. temperatureto reflux (120 C) for 90 minutes to completion
3. customaffording a dark red solution
4. concentrationThe mixture was concentrated in vacuo
5. additionThe residue was poured into ice water
6. extractionThe acidic melt was extracted with ether
7. washThe organic was washed with cold water, cold half saturated NaHCO3 solution, brine
8. customseparated
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-c6c30e334e374ded912c57d65d5515db

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680114B2