Triethylamine → 2-Amino-3,6-dibromopyrazine

Diphenylphosphorylazide (2.59 mL, 12 mmol) and triethylamine (1.67 mL, 12 mmol) are added to a solution of 3,6-dibromo-pyrazin-2-carboxylic acid (3.52 g, 12 mmol) in t-butanol (90 mL). The reaction is heated at reflux for 18 hours. The reaction is quenched with water, then concentrated in vacuo and taken up in DCM. The organic solution is washed with water and 1N NaOH, dried over MgSO4 and concentrated in vacuo. The resultant solid is filtered through a pad of silica using EtOAc, then concentrated and TFA:DCM (4:1, 12 mL) is added to the solid and stirred for 30 min. The solution is concentrated in vacuo then neutralised with 1N NaOH and extracted with DCM. The organic layer is dried over anhydrous MgSO4 and concentrated in vacuo to give the product. 1H NMR (250 MHz, DMSO-d6) δ(ppm) 7.25 (br s, 2H), 7.68 (s, 1H); m/z (APCI) 254 (M+H)+; m.p 135-139° C.

1. temperatureThe reaction is heated
2. temperatureat reflux for 18 hours
3. customThe reaction is quenched with water
4. concentrationconcentrated in vacuo
5. washThe organic solution is washed with water and 1N NaOH
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. filtrationThe resultant solid is filtered through a pad of silica
9. concentrationconcentrated
10. additionTFA:DCM (4:1, 12 mL) is added to the solid
11. concentrationThe solution is concentrated in vacuo
12. extractionextracted with DCM
13. dry with materialThe organic layer is dried over anhydrous MgSO4
14. concentrationconcentrated in vacuo
15. customto give the product
16. customm.p 135-139° C.

ORD-Eintrag

ord-f1ff70b0333c4601bfd6669ba7bb24cd

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08012983B2