Triethylamine → 4-Chloro-5-fluoro-6-hydrazino-2-(methylthio)pyrimidine

Temperatur

5 °C

4,6-Dichloro-5-fluoro-2-(methylthio)pyrimidine (16.8 g, 78.85 mmol) and triethylamine (16.49 mL, 118.3 mmol) were dissolved in DMSO (200 mL) and stirred. The mixture was cooled to ˜5° C. with an ice water bath. To this solution was slowly added hydrazine monohydrate (4.59 mL, 94.62 mmol). After the addition was complete, the reaction mixture was warmed up to RT and stirring was continued for 1 h. The reaction mixture was diluted with water (500 mL), and the aqueous solution was extracted with CH2Cl2 (3×300 mL). The combined organic solution was washed with water (3×250 mL) and brine (250 mL), then dried (Na2SO4) and concentrated in vacuo to afford 4-chloro-5-fluoro-6-hydrazino-2-(methylthio)pyrimidine as a red foamy solid (9.70 g, 59%). LCMS: (M+H)+: 208.9.

1. additionAfter the addition
2. temperaturethe reaction mixture was warmed up to RT
3. stirringstirring
4. extractionthe aqueous solution was extracted with CH2Cl2 (3×300 mL)
5. washThe combined organic solution was washed with water (3×250 mL) and brine (250 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo

ORD-Eintrag

ord-ac801d8532914b6f9d5ae02facebb00e

Quelldatensatz

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07893056B2