Cycloheptanol → 4-Chloro-6-(cycloheptyloxy)pyrimidine

HRID 1759997Notes

Reaction equation

HRID 1759997 reaction equation
[H-].[Na+].[CH:3]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[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:10][CH:3]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 10399CycloheptanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 225996844-Chloro-6-(cycloheptyloxy)pyrimidineYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 1 ml of a tetrahydrofuran solution containing 0.25 g of cycloheptanol was slowly added dropwise with stirring at 0° C. The mixture was stirred at 0° C. for 10 minutes, to which 1 ml of a tetrahydrofuran solution containing 0.3 g of 4,6-dichloropyrimidine was added at 0° C., followed by further stirring for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with t-butyl methyl ether. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.43 g of 4-chloro-6-cycloheptyloxypyrimidine.

Workup

  1. additionwas slowly added dropwise
  2. additionwas added at 0° C.
  3. stirringby further stirring for 2 hours
  4. extractionextracted three times with t-butyl methyl ether
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-734ed1f0286a4f4eaff05543cd1ed33a
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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