Hydrochloric Acid → 2-chloro-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one

A solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (400 mg, 2.13 mmol) in a 2M aqueous potassium hydroxide solution (12 mL) was heated to 100° C. for 4 h. At this time, the resulting mixture was poured onto iced water and then acidified to pH 6.5 with a 6M aqueous hydrochloric acid solution. The acidic solution was extracted with ethyl acetate. The combined organics were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was triturated with acetonitrile and ether to afford 2-chloro-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one. 1HNMR (400 MHz, DMSO-d6) δ ppm 6.40-6.48 (m, 1H) 7.01-7.10 (m, 1H) 12.0 (s, 1H) 12.8 (s, 1H).

1. extractionThe acidic solution was extracted with ethyl acetate
2. washThe combined organics were washed with a saturated aqueous sodium chloride solution
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe resulting residue was triturated with acetonitrile and ether

ORD record

ord-64ae9a8eba774b508171f4317abd3e2c

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722661B2