Sodium hydride → HCID 66668642, compound

To a solution of 1H-1,2,3-triazole (63.2 mg, 0.915 mmol) in THF (2.4 mL), was added, portionwise, at 0° C., NaH (39.9 mg, 0.998 mmol). After 30 minutes of stirring, 4-chloro-5-iodopyrimidine (200 mg, 0.832 mmol) was added and the reaction mixture was allowed to come to room temperature, and stirred until judged complete by LCMS. To this was added aqueous saturated NH4Cl, and the mixture was allowed to stir for 5 min at which time it was determined that the reaction was complete by LC-MS analysis. This reaction mixture was diluted with ethyl acetate and extracted twice. The combined organics were washed with brine and dried over Na2SO4, filtered and concentrated in vacuo. The crude material was dissolved in a minimal amount of hexanes and loaded onto a silica gel column, the column was subsequently eluted as a gradient from 0-15% EtOAc/hexanes. The desired isomer was thus separated from the regioisomeric triazole adduct. The white solid attained (90 mg, 39.6%) was determined to be the desired material by 1HNMR and LC/MS. MS (ES): m/z=274.0 [M+H]+. 1H NMR (400 MHz, CCl3D) δ ppm 9.34 (1 H, s), 9.15 (1 H, s), 8.03 (2 H, s).

1. customat 0° C.
2. customto come to room temperature
3. stirringstirred
4. stirringto stir for 5 min at which time it
5. extractionextracted twice
6. washThe combined organics were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. dissolutionThe crude material was dissolved in a minimal amount of hexanes
11. washthe column was subsequently eluted as a gradient from 0-15% EtOAc/hexanes
12. customThe desired isomer was thus separated from the regioisomeric triazole adduct

ORD record

ord-359101450e9644d4820f48760686a3f5

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673922B2