Ethyl Acetate → 1,1-Dimethylethyl 2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)hydrazinecarboxylate

2,4,6-Trichloro-5-fluoropyrimidine (20.92 g, 104.1 mmol) was dissolved in THF (300 mL) at room temperature and stirred. To this stirring solution was added t-butyl carbazate (13.74 g, 104.1 mmol), followed by diisopropylethylamine (19.0 mL, 109.3 mmol). The reaction mixture turned light yellow, and after several minutes a precipitate formed. The reaction appeared complete after 1.5 h, as monitored by TLC (10% EtOAc/Hex). The reaction mixture was concentrated in vacuo to remove most of the THF, and the residue was dissolved in CH2Cl2 (˜400 mL). The solution was washed with ˜400 mL of sat. aq. NH4Cl. The organics were dried and concentrated to give a pale yellow solid (31.37 g). LCMS: (M+H+2Na-Boc)+: 241.

1. customafter several minutes a precipitate formed
2. concentrationThe reaction mixture was concentrated in vacuo
3. customto remove most of the THF
4. dissolutionthe residue was dissolved in CH2Cl2 (˜400 mL)
5. washThe solution was washed with ˜400 mL of sat. aq. NH4Cl
6. customThe organics were dried
7. concentrationconcentrated

ORDレコード

ord-543f4d8f1678433ebc25c457074b7ada

出典データセット

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07893056B2