Sodium hydride → HCID 18366572, compound

HRID 379537Notes

Reaction equation

HRID 379537 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl[C:18]1[C:23]([Cl:24])=[C:22]([CH2:25][CH3:26])[N:21]=[CH:20][N:19]=1>O1CCCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][C:18]2[C:23]([Cl:24])=[C:22]([CH2:25][CH3:26])[N:21]=[CH:20][N:19]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 111376684,5-Dichloro-6-ethylpyrimidine

Product 1

HCID 18366572HCID 18366572, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.4 g (10 mmol) of sodium hydride (80% dispersion in oil) was added to a solution of 2.0 g (10 mmol) of 1-(tert-butoxycarbonylpiperidin-4-ol and 1.8 g (10 mmol) of 4,5-dichloro-6-ethylpyrimidine in 25 ml of tetrahydrofuran, and the mixture was stirred for 2 hours at room temperature for 1 hour at reflux. After cooling, the mixture was concentrated, the residue was taken up in water/toluene, and the organic phase was dried and concentrated. For purification, the product was chromatographed on silica gel (petroleum ether/ethyl acetate 7:3). This gave 2.5 g (73.5% of theory) of a yellow oil.

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. customthe organic phase was dried
  5. concentrationconcentrated
  6. customFor purification
  7. customthe product was chromatographed on silica gel (petroleum ether/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-9928fc2bbafc4627a045041ec19ca999
Source dataset
uspto-grants-2001_10
Patent number
US06300333B1

Reaction notes

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