Ethyl 4-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxylate → (4-(Isopropylamino)-2-(methylthio)pyrimidin-5-yl)methanol
Reaktionsgleichung
[CH:1]([NH:4][C:5]1[C:10]([C:11](OCC)=[O:12])=[CH:9][N:8]=[C:7]([S:16][CH3:17])[N:6]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]([NH:4][C:5]1[C:10]([CH2:11][OH:12])=[CH:9][N:8]=[C:7]([S:16][CH3:17])[N:6]=1)([CH3:3])[CH3:2]Komponenten
4
Versuchsvorschrift
To a solution of ethyl 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylate (16.4 g, 64.4 mmol) in anhydrous THF (100 mL) was added LAH (6.1 g, 0.16 mol) in portions at 0° C. under N2 atmosphere, then the reaction mixture was stirred at r.t. for 30 min. The reaction was quenched by the addition of water (6 mL) followed by aqueous solution of 2N NaOH (6 mL). The suspension was filtered and the filtrate was concentrated to give (4-(isopropylamino)-2-(methylthio)pyrimidin-5-yl)methanol (13.5 g, 98.4% yield), which was used in next step without further purification. 1HNMR (400 MHz, DMSO-d6): δ 7.79 (s, 1 H), 6.37 (d, J=7.6 Hz, 1 H), 5.10 (t, J=5.6 Hz, 1 H), 4.28-4.20 (m, 3 H), 2.38 (s, 3 H), 1.13 (d, J=6.4 Hz, 6 H).