1-Chloro-2-iodoethane → 5-(2-Ethylbenzoimidazol-1-yl)-2-iodo-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine

温度

-5 °C

A solution of 5 -(2-ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine (1.92 g, 5.23 mmol) in THF (60 mL) was cooled to −40° C. before the drop wise addition of LiHMDS (6.3 mL, 6.28 mmol, 1 M solution in THF). The resulting mixture was warmed to −5° C. over 30 min then mixture was cooled back to −30° C. before the addition of a solution of 1-chloro-2-iodoethane (2.0 g, 10.47 mmol) in THF (6 mL) The resulting mixture was allowed to warm to 0° C. then quenched with NH4Cl and extracted with EtOAc. The combined organics were washed with brine then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, EtOAc:DCM, 50-80%) followed by recrystallisation from iPrOAc affording the title compound as a yellow solid (1.58 g, 62%)._LCMS (method A): RT 3.50 min [M+H]+ 493.0

1. temperatureto warm to 0° C.
2. customthen quenched with NH4Cl
3. extractionextracted with EtOAc
4. washThe combined organics were washed with brine
5. dry with materialthen dried (Na2SO4)
6. concentrationconcentrated in vacuo
7. customThe resulting residue was purified by column chromatography (Si—PCC, EtOAc:DCM, 50-80%)
8. customfollowed by recrystallisation from iPrOAc affording the title compound as a yellow solid (1.58 g, 62%)
9. customRT 3.50 min [M+H]+ 493.0

ORDレコード

ord-2995dab65c564bfe9440a6e3e763c92e

出典データセット

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08173650B2