Thionyl Chloride → (2-Chloro-6-methylpyrimidin-4-yl)methanol

Temperatur

60 °C

5.00 g (28.97 mmol) of 2-chloro-6-methylpyrimidine-4-carboxylic acid and 5.17 g (118.97 mmol) of thionyl chloride are initially charged in 60 ml of dry toluene and stirred at 60° C. for 3 h. The reaction solution is concentrated on a rotary evaporator, 20 ml of toluene are added to the residue and the mixture is again concentrated to dryness on a rotary evaporator. The residue is dissolved in 40 ml of methyl tert-butyl ether and cooled to 5° C. At this temperature, a solution of 2.41 g (63.74 mmol) of sodium borohydride in 40 ml of water is added. After warming to RT, the reaction mixture is kept at 4° C. for 24 h. 40 ml of ethyl acetate and 10 ml of sat. sodium bicarbonate solution are then added to the mixture. The organic phase is washed twice with in each case 10 ml of water. After drying of the organic phase over magnesium sulphate, the solvent is removed on a rotary evaporator.

1. concentrationThe reaction solution is concentrated on a rotary evaporator, 20 ml of toluene
2. additionare added to the residue
3. concentrationthe mixture is again concentrated to dryness on a rotary evaporator
4. dissolutionThe residue is dissolved in 40 ml of methyl tert-butyl ether
5. temperaturecooled to 5° C
6. temperatureAfter warming to RT
7. waitthe reaction mixture is kept at 4° C. for 24 h
8. washThe organic phase is washed twice with in each case 10 ml of water
9. dry with materialAfter drying of the organic phase over magnesium sulphate
10. customthe solvent is removed on a rotary evaporator

ORD-Eintrag

ord-271ac424dc3f4c8ba4ec4113e4d70e88

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08653109B2