3-Iodoaniline → HCID 57962262, compound

Temperature

120 °C

A solution of 2,4-dichloropyrimidine (3.0 g, 20 mmol) and N,N-diisopropylethylamine (4.2 mL, 24 mmol) in N-methylpyrrolidinone (20 mL) was treated with 3-iodoaniline (2.4 mL, 20 mmol) dropwise and heated at 120° C. for 2 h. The reaction mixture was concentrated, diluted with ethyl acetate (150 mL), and washed with water (150 mL). The aqueous layer was separated and extracted with ethyl acetate (150 mL). The combined organic extracts were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to a crude oil. This material was purified by flash column chromatography to give the desired product (3.2 mg, 48%) as a tan solid. LCMS for C10H8ClIN3 (M+H)+: m/z=331.9.

1. concentrationThe reaction mixture was concentrated
2. additiondiluted with ethyl acetate (150 mL)
3. washwashed with water (150 mL)
4. customThe aqueous layer was separated
5. extractionextracted with ethyl acetate (150 mL)
6. washThe combined organic extracts were washed with brine (100 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated to a crude oil
10. customThis material was purified by flash column chromatography

ORD record

ord-c56337ccb33e4ac7b41a99573dc35955

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871753B2