2,4-dimethylpentan-3-ol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a four-neck flask having an inner volume of 100 ml, 5.81 g (50 m.mols) of 2,4-dimethyl-3-pentanol, 6.30 g (55 m.mols) of methane sulfonyl chloride, and 50 ml of methylene chloride were placed and cooled to 0° C. To the cooled mixture, 7.59 g (75 m.mols) of triethyl amine was added dropwise over a period of one hour with the reaction temperature retained meanwhile. The reactants in the resultant reaction mixture were left reacting at 0° C. for one hour. After the reaction, the reaction mass was thrown into 50 ml of ice water to obtain an organic layer by separation. The organic layer thus obtained was washed with 50 ml of a diluted aqueous hydrochloric acid solution, 50 ml of water, 50 ml of a saturated aqueous sodium hydrogen carbonate solution, and 50 ml of a saturated saline solution. Then, by removing the solvent from the organic layer, 8.94 g (46 m.mols) of (2,4-dimethyl-3-pentyl) methanesulfonate was obtained as the product aimed at. In a four-neck flask having The reactants in the resultant reaction mixture were left After the reaction to obtain an organic layer by separation The organic layer thus obtained was washed with 50 ml of a diluted aqueous hydrochloric acid solution, 50 ml of water, 50 ml of a saturated aqueous sodium hydrogen carbonate solution, and 50 ml of a saturated saline solution Then, by removing the solvent from the organic layer

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a four-neck flask having an inner volume of 100 ml, 5.81 g (50 m.mols) of 2,4-dimethyl-3-pentanol, 6.30 g (55 m.mols) of methane sulfonyl chloride, and 50 ml of methylene chloride were placed and cooled to 0° C. To the cooled mixture, 7.59 g (75 m.mols) of triethyl amine was added dropwise over a period of one hour with the reaction temperature retained meanwhile. The reactants in the resultant reaction mixture were left reacting at 0° C. for one hour. After the reaction, the reaction mass was thrown into 50 ml of ice water to obtain an organic layer by separation. The organic layer thus obtained was washed with 50 ml of a diluted aqueous hydrochloric acid solution, 50 ml of water, 50 ml of a saturated aqueous sodium hydrogen carbonate solution, and 50 ml of a saturated saline solution. Then, by removing the solvent from the organic layer, 8.94 g (46 m.mols) of (2,4-dimethyl-3-pentyl) methanesulfonate was obtained as the product aimed at. In a four-neck flask having The reactants in the resultant reaction mixture were left After the reaction to obtain an organic layer by separation The organic layer thus obtained was washed with 50 ml of a diluted aqueous hydrochloric acid solution, 50 ml of water, 50 ml of a saturated aqueous sodium hydrogen carbonate solution, and 50 ml of a saturated saline solution Then, by removing the solvent from the organic layer

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

Procedure: 2,4-Dimethyl-3-pentanol (29 g, 0.25 mole), dissolved in formic acid (98%, 46 g, 1 mole), was added dropwise over one hour to a rapidly-stirred, ice-cooled mixture of formic acid (98%, 3 ml) and concentrated sulfuric acid (270 ml). During the addition the reaction mixture foamed vigorously and was stirred for a further one hour at 10°-20° C. The mixture was poured on to ice (1 kg) and the resulting solution extracted with hexanes (3×200 ml). The combined organic phases were extracted with 2N potassium hydroxide (2×200 ml) plus ice (50 g) and the aqueous extracts washed with hexanes (100 ml). The aqueous phase was then acidified (pH 2) and the product extracted into hexanes (3×200 ml). After washing with saturated sodium chloride and drying (MgSO4), the solution was evaporated under reduced pressure and the residue distilled to give 2,2,4-trimethylpentanoic acid (36 g). was added dropwise over one hour to a rapidly-stirred, ice- cooled During the addition the reaction mixture the resulting solution extracted with hexanes (3×200 ml) The combined organic phases were extracted with 2N potassium hydroxide (2×200 ml) plus ice (50 g) the aqueous extracts washed with hexanes (100 ml) the product extracted into hexanes (3×200 ml) After washing with saturated sodium chloride drying (MgSO4) the solution was evaporated under reduced pressure the residue distilled

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

Procedure: In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.23 g of 2,4-dimethyl-3-pentanol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was 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 0.17 g of 2-butyn-1-ol in tetrahydrofuran at room temperature and further added 0.11 g of sodium hydride (60% in oil), followed by stirring 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 0.44 g of 4-(2-butynyloxy)-6-(1-isopropyl-2-methylpropyloxy)pyrimidine (the present compound (30)). was added dropwise at 0° C. by stirring at the same temperature for 3 hours by stirring 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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a four-neck flask having an inner volume of 100 ml, 5.81 g (50 m.mols) of 2,4-dimethyl-3-pentanol, 6.30 g (55 m.mols) of methane sulfonyl chloride, and 50 ml of methylene chloride were placed and cooled to 0° C. To the cooled mixture, 7.59 g (75 m.mols) of triethyl amine was added dropwise over a period of one hour with the reaction temperature retained meanwhile. The reactants in the resultant reaction mixture were left reacting at 0° C. for one hour. After the reaction, the reaction mass was thrown into 50 ml of ice water to obtain an organic layer by separation. The organic layer thus obtained was washed with 50 ml of a diluted aqueous hydrochloric acid solution, 50 ml of water, 50 ml of a saturated aqueous sodium hydrogen carbonate solution, and 50 ml of a saturated saline solution. Then, by removing the solvent from the organic layer, 8.94 g (46 m.mols) of (2,4-dimethyl-3-pentyl) methanesulfonate was obtained as the product aimed at. In a four-neck flask having The reactants in the resultant reaction mixture were left After the reaction to obtain an organic layer by separation The organic layer thus obtained was washed with 50 ml of a diluted aqueous hydrochloric acid solution, 50 ml of water, 50 ml of a saturated aqueous sodium hydrogen carbonate solution, and 50 ml of a saturated saline solution Then, by removing the solvent from the organic layer