Sodium hydride → HCID 17979091, compound

HRID 1354103Notes

Reaction equation

HRID 1354103 reaction equation
[H-].[Na+].[CH:3]1([CH:6]([OH:8])[CH3:7])[CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:15]=[C:14](Cl)[N:13]=[CH:12][N:11]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:9][C:10]1[CH:15]=[C:14]([O:8][CH:6]([CH:3]2[CH2:5][CH2:4]2)[CH3:7])[N:13]=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 791041-Cyclopropylethanol

Product 1

HCID 17979091HCID 17979091, compound

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 0.5 ml of a solution containing 0.19 g of 1-cyclopropylethanol in tetrahydrofuran was added dropwise at room temperature. After stirring at room temperature for 10 minutes, 0.5 ml of a solution containing 0.3 g of 4,6-dichloropyrimidine in tetrahydrofuran was added dropwise at 0° C., followed by stirring at the same 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 to give a crude product of 4-chloro-6-(1-cyclopropylethoxy)pyrimidine.

Workup

  1. additionwas added dropwise at room temperature
  2. additionwas added dropwise at 0° C.
  3. stirringby stirring at the same temperature 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-3bb3959afcd94dc0827ecc57ec0ea429
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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