2,4-Dimethyl-3-pentanol → 4-(2-Butynyloxy)-6-(1-isopropyl-2-methylpropyloxy)pyrimidine

HRID 1354133Notes

Reaction equation

HRID 1354133 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH:6]([OH:10])[CH:7]([CH3:9])[CH3:8])[CH3:5].Cl[C:12]1[CH:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1.[CH2:19]([OH:23])[C:20]#[C:21][CH3:22].[Cl-].[NH4+]>O1CCCC1>[CH2:19]([O:23][C:12]1[CH:17]=[C:16]([O:10][CH:6]([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:5])[CH3:3])[N:15]=[CH:14][N:13]=1)[C:20]#[C:21][CH3:22]

Participants

7

Reactant 5

HCID 117522,4-Dimethyl-3-pentanolHCID 129912-Butyn-1-olHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 179790964-(2-Butynyloxy)-6-(1-isopropyl-2-methylpropyloxy)pyrimidineYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

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)).

Workup

  1. additionwas added dropwise at 0° C.
  2. stirringby stirring at the same temperature for 3 hours
  3. stirringby stirring for 4 hours
  4. extractionwas extracted three times with t-butyl methyl ether
  5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-791a9931e6334803b96d0078bc59cd7d
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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