N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-7-(2,4-difluorophenyl)-N4-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine → (R)-N2-(4-(4-Chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-7-(2,4-difluorophenyl)-N4-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine

A racemic mixture of N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-N4-trideuteromethyl-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine (180 mg, 0.206 mmol from Example 109) was purified using chiral supercritical fluid chromatography (SFC) to afford 28.4 mg of peak A (Example 109A) and 27.4 mg of peak B (Example 109B). SFC Method: Chiralpak OJ-H (21×250 mm, 5 μM), 35% methanol (0.1% diethylamine) in CO2, 35° C., flow rate 45 mL/min for 10 min, absorbance 268 nm, injection 0.75 mL of 20 mg/mL solution in methanol (multiple stacked injections), tR (peak A)=3.6 min, tR (peak B) 7.2 min. The absolute stereochemistry of individual enantiomers (Examples 109A and 109B) was not determined LC-MS and 1H NMR analytical data for the separated enantiomers was identical to the racemate (Example 109).