Ethyl Acetate → 4-Chloro-5-(cyclopropylmethoxy)-2-methylsulfanylpyrimidine

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Reaktionsgleichung

[CH:1]1([CH2:4][O:5][C:6]2[C:7](O)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=2)[CH2:3][CH2:2]1.O=P(Cl)(Cl)[Cl:17].CC(=O)OCC>CC#N>[Cl:17][C:7]1[C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[CH:11][N:10]=[C:9]([S:12][CH3:13])[N:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To the title compound of step 2 (29.00 g, 136.79 mmol) and N(CH3)4C1 (22.47 g, 205.19 mmol) in anhydrous MeCN (300 mL), was added POCl3 (123.93 g, 820.74 mmol). The mixture was stirred at r.t. for 30 min and at 70° C. for 1 h. After concentration under vacuum, EA extractive work up and silica gel chromatography (PE:EA=50:1-5:1) gave the title compound (20 g, 63.6% yield) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.16 (s, 1H), 3.95 (d, J=6.8 Hz, 2H), 2.56 (s, 3H), 1.33-1.28 (m, 1H), 0.72-0.70 (m, 2H), 0.41-0.37 (m, 2H). LCMS: 230.9 (M+1)+

Aufarbeitung

concentrationAfter concentration under vacuum, EA extractive work up

Quellen und Nachweise

ORD-Eintrag: ord-5587f2481fb446c5b57936c3cc306adb
Quelldatensatz: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09034900B2

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