Application of 13036-50-5 ,Some common heterocyclic compound, 13036-50-5, molecular formula is C10H7ClN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a solution of 2,4-dichloropyrimidine (149 mg, 1 mmol) in THF (5 mL), tetrakis (triphenylphosphine) palladium (23 mg, 2 mol%) and 0.5M solution of phenylzinc bromide (2.1 mL, 1.05 mmol) in THF were added. The reaction mixture was stirred at50 C for overnight. Then it was added saturated ammonium chloride solution and extracted with EtOAc twice. The organic layers were combined, washed with water and dried(MgS04). Evaporation of solvent gave a yellow residue which was purified by Prep. HPLC to afford a yellowish oil as 2-chloro-4-phenyl- pyrimidine to carry on. To a solution of intermediate 2 (20 mg, 0.039 mmol) in DMF (3 mL), NaH (3.9 mg of 60% dispersion in mineral oil, 0.0975 mmol) was added at0 C. The reaction mixture was then warmed to rt. and stirred for 1 hr. Then 2-chloro-4-phenyl- pyrimidine prepared above (18 mg as crude) was added. The reaction mixture was stirred at rt. for overnight. It was then quenched with water and extracted with EtOAc. The organic layer was separated, washed with brine and dried(MgS04). Evaporation of solvent gave yellowish oil which was then purified by Prep. HPLC to give a thick colorless oil as final product (Compound 335) as TFA salt. (5.5 mg, 18% yield) ‘H NMR (CD30D, 300 MHz) 0.92-1. 12 (m, 11 H). 1.25 (m, 2 H), 1.44 (dd, J=9. 2, 5.5 Hz,1 H), 1.89 (dd, J=8. 1,5. 5 Hz, 1H), 2.17-2. 37 (m, 2 H), 2.57 (m, 1 H), 2.95 (m,1 H), 3.52 (s, 3 H), 4.14 (m,1 H), 4.24-4. 38 (m, 2 H), 4.51 (m,1 H), 5.13 (d, J=10. 2 Hz,1 H), 5.31 (d, J=17. 2 Hz,1 H), 5.77 (m,1 H), 5.86 (s,1 H), 7.48-7. 60 (m,3 H), 7.66 (d, J=5.3 Hz, 1 H), 8.18 (m,2 H), 8.60 (d, J=5.1 Hz, 1 H). LC-MS (retention time: 1.947 min. ), MS m/z 669(MH+).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 13036-50-5, 2-Chloro-4-phenylpyrimidine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99274; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia