Methallyl alcohol → HCID 17979065, compound

HRID 1354163Notes

Reaction equation

HRID 1354163 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[C:4]#[C:5][CH2:6][CH3:7].Cl[C:10]1[CH:15]=[C:14](Cl)[N:13]=[CH:12][N:11]=1.[CH3:17][C:18](=[CH2:21])[CH2:19][OH:20].[Cl-].[NH4+]>O1CCCC1>[CH3:21][C:18](=[CH2:17])[CH2:19][O:20][C:10]1[CH:15]=[C:14]([O:8][CH2:3][C:4]#[C:5][CH2:6][CH3:7])[N:13]=[CH:12][N:11]=1

Participants

7

Reactant 5

HCID 10557Methallyl alcoholHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 804212-Pentyn-1-ol

Product 1

HCID 17979065HCID 17979065, compoundYield 136.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

In 10 ml of tetrahydrofuran was suspended 0.19 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.57 g of 2-pentyn-1-ol in tetrahydrofuran was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution con-taining 0.3 g of 4,6-dichloropyrimidin in tetrahydrofuran at 0° C., followed by stirring for 1 hour. To this was added dropwise 0.5 ml of a solution containing 0.48 g of 2-methyl-2-propen-1-ol in tetrahydrofuran at the same temperature and further added 0.19 g of sodium hydride (60% in oil), followed by stirring at 2 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 0.64 g of 4-(2-methyl-2-propenyloxy)-6-(2-pentynyloxy)pyrimidine.

Workup

  1. additionwas added dropwise at room temperature
  2. stirringby stirring for 1 hour
  3. stirringby stirring at 2 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-d80dd0a400364994bacb6b8dd2c6db4e
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

Loading…