3-methylpentan-2-ol

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-methylpentan-2-ol (0.18 mL) in toluene (4 mL) was added sodium hydride (0.14 g), and the resulting mixture was stirred at 70° C. for 15 min under a nitrogen atmosphere. A mixture of tert-butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.50 g), BINAP (0.033 g), Pd2(dba)3 (0.024 g) and toluene (4 mL) was added, and the resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane) to give tert-butyl 8-(1,2-dimethylbutoxy)-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.37 g, 61%) as a yellow oil. was added the resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere the resulting product was extracted with ethyl acetate The organic layer was washed with water and saturated brine dried the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane)

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

Procedure: 3-Methyl-pentan-2-ol (400 g), crotonic acid (CH3CH═CHCOOH) (445.5 g), toluene (400 mL), and para-toluenesulfonic acid (PTSA) (4 g) were charged into to 2-L reaction flask fitted with a mechanical stirrer, a thermocouple, a condenser, and a Bidwell-Sterling trap. The reaction mixture was heated to reflux. Water was collected and removed via the Bidwell-Sterling trap. The reaction mixture was aged for about 3.5 hours. The resulting reaction mixture was then cooled and washed sequentially with water, aqueous sodium hydroxide (NaOH) (10%), and brine. The aqueous and organic layers were split. The organic layer was fractional distilled to provide but-2-enoic acid 1,2-dimethyl-butyl ester (444 g) with a boiling point of 106° C. at 34 mmHg. fitted with a mechanical stirrer The reaction mixture was heated to reflux Water was collected removed via the Bidwell-Sterling trap The resulting reaction mixture was then cooled washed sequentially with water, aqueous sodium hydroxide (NaOH) (10%), and brine The aqueous and organic layers were split The organic layer was fractional distilled

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

Procedure: In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.21 g of 3-methyl-2-pentanol in tetrahydrofuran was added dropwise at 0° C., followed by stirring for 10 minutes. To this was slowly added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 3 hours. To this was added dropwise 0.4 ml of a solution containing 0.14 g of 2-butyn-1-ol at 0° C. and further added 0.10 g of sodium hydride (60% in oil), followed by further stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.29 g of 4-(2-butynyloxy)-6-(1,2-dimethylbutyloxy)pyrimidine (the present compound (16)). was added dropwise at 0° C. by stirring at the same temperature for 3 hours by further stirring at room temperature for 4 hours was extracted three times with t-butyl methyl ether The combined organic layers were washed with a saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate concentrated