Sodium hydride → HCID 17979072, compound

HRID 1354154Notes

Reaction equation

HRID 1354154 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]([O:9][CH3:10])[CH:6]([OH:8])[CH3:7].[Cl:11][C:12]1[CH:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([O:8][CH:6]([CH3:7])[CH:5]([O:9][CH3:10])[O:4][CH3:3])[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 5543781,1-Dimethoxy-2-propanol

Product 1

HCID 17979072HCID 17979072, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 5 ml of tetrahydrofuran was suspended 0.13 g of sodium hydride (60% in oil), to which 5.4 ml of a 0.5 mol/l solution containing 1,1-dimethoxy-2-propanol in tetrahydrofuran was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.4 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at 0° C. 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 0.16 g of 4-chloro-6-(2,2-dimethoxy-1-methylethoxy)pyrimidine.

Workup

  1. additionwas added dropwise at 0° C.
  2. dissolutiondissolved
  3. stirringby stirring at 0° C. 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-333b7a01c2d94ff7829ee5aa6c9cb98c
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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