(2S)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-amine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A procedure similar to that described in Preparation 9 was repeated, except that 10.22 g of benzyl N-[2-t-butyldimethylsilyloxy-1(S)-methylethyl]carbamate (prepared as described in Preparation 32), 2.00 g of 10% w/w palladium-on-carbon and 80 ml of ethanol were used, to give 5.69 g of the title compound having an Rf value of 0.27 (on silica gel thin layer chromatography, using a 1:3 by volume mixture of ethyl acetate and hexane as the developing solvent) and having [α]D =+9.7° (methanol, c=1.040). A procedure similar to that described in Preparation 9

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A procedure similar to that described in Preparation 9 was repeated, except that 10.22 g of benzyl N-[2-t-butyldimethylsilyloxy-1(S)-methylethyl]carbamate (prepared as described in Preparation 32), 2.00 g of 10% w/w palladium-on-carbon and 80 ml of ethanol were used, to give 5.69 g of the title compound having an Rf value of 0.27 (on silica gel thin layer chromatography, using a 1:3 by volume mixture of ethyl acetate and hexane as the developing solvent) and having [α]D =+9.7° (methanol, c=1.040). A procedure similar to that described in Preparation 9

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-2-tert-Butyldimethylsilyloxy-1-methylethylamine (120 g, 636 mmol) was added to (4,6-dichloropyrimidin-5-yl)acetaldehyde (52.8 g, 276 mmol) in ethanol (500 mL). The mixture was heated to reflux for 45 minutes. The reaction mixture was evaporated in vacuo then the residue was diluted with water (400 mL) and extracted with ethyl acetate (600 mL). The organic extract was evaporated in vacuo and the crude material was purified by column chromatography on silica gel (gradient of pentane:EtOAc 90:10 to 80:20) to afford the title compound as a yellow liquid in 67% yield, 60.4 g. The mixture was heated to reflux for 45 minutes The reaction mixture was evaporated in vacuo the residue was diluted with water (400 mL) extracted with ethyl acetate (600 mL) The organic extract was evaporated in vacuo the crude material was purified by column chromatography on silica gel (gradient of pentane:EtOAc 90:10 to 80:20)