Sodium Carbonate → (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine 1-oxide

m-CPBA (8.30 g, 37.0 mmol) was added in three portions to a solution of (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (2.5 g, 14.8 mmol) in CHCl3 (60 mL). The mixture was stirred at room temperature for 2 days. The mixture was cooled to 0° C., and Na2S2O3 (10 g) in water (60 mL) was added dropwise. Na2CO3 (6 g) in water (20 mL) was then added. The reaction mixture was stirred for 20 minutes. The aqueous phase was extracted with CHCl3 (2×200 mL), and the combined organic phases were concentrated at low temperature (<25° C.). The residue was purified by silica gel chromatography, eluting with ethyl acetate-DCM/MeOH (20:1) to give (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-oxide (1.45 g, 53%). 1H NMR (CDCl3, 400 MHz) δ 8.66 (s, 1H), 3.50 (m, 1H), 3.20 (m, 2H), 2.44 (m, 1H), 1.90 (m, 1H), 1.37 (d, J=7.2 Hz, 3H).

1. temperatureThe mixture was cooled to 0° C.
2. stirringThe reaction mixture was stirred for 20 minutes
3. extractionThe aqueous phase was extracted with CHCl3 (2×200 mL)
4. concentrationthe combined organic phases were concentrated at low temperature (<25° C.)
5. customThe residue was purified by silica gel chromatography
6. washeluting with ethyl acetate-DCM/MeOH (20:1)

ORD record

ord-59f388261ad44d5d8dcaf1f44d14253c

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846683B2