Methyl iodide → HCID 17979080, compound

HRID 1354134Notes

Reaction equation

HRID 1354134 reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[C:8]([O:10][CH:11]([CH3:16])[C:12]([OH:15])([CH3:14])[CH3:13])[N:7]=[CH:6][N:5]=1.I[CH3:18].[CH2:19]([OH:23])[C:20]#[C:21][CH3:22].[Cl-].[NH4+]>O1CCCC1>[CH2:19]([O:23][C:4]1[CH:9]=[C:8]([O:10][CH:11]([CH3:16])[C:12]([O:15][CH3:18])([CH3:14])[CH3:13])[N:7]=[CH:6][N:5]=1)[C:20]#[C:21][CH3:22]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 129912-Butyn-1-olHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 17979112HCID 17979112, compound

Product 1

HCID 17979080HCID 17979080, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 2 ml of tetrahydrofuran was suspended 0.03 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.26 g of 4-chloro-6-(2-hydroxy-1,2-dimethylpropyloxy)pyrimidine was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.3 ml of a solution containing 0.11 g of iodomethane in tetrahydrofuran, followed by further stirring at the same temperature for 4 hours. To this was added dropwise 0.3 ml of a solution containing 0.06 g of 2-butyn-1-ol in tetrahydrofuran at room temperature and further added 0.03 g of sodium hydride (60% in oil), followed by stirring for 5 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 0.04 g of 4-(2-butynyloxy)-6-(2-methoxy-1,2-dimethylpropyloxy)pyrimidine (the present compound (31)).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringby further stirring at the same temperature for 4 hours
  3. stirringby stirring for 5 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-e4f8d0a3631a45b49b93537f90a0cf7e
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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