Sodium hydride → 4-Chloro-6-(2-ethylpiperidino)-5-fluoropyrimidine

HRID 1008726Notes

Reaction equation

HRID 1008726 reaction equation
[H-].[Na+].[CH2:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][NH:6]1)[CH3:4].[Cl:11][C:12]1[C:17]([F:18])=[C:16](Cl)[N:15]=[CH:14][N:13]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:11][C:12]1[C:17]([F:18])=[C:16]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]2[CH2:3][CH3:4])[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 942052-EthylpiperidineHCID 112866754,6-Dichloro-5-fluoropyrimidine

Product 1

HCID 593411174-Chloro-6-(2-ethylpiperidino)-5-fluoropyrimidineYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.07 g of sodium hydride (60% oil suspension) was suspended in 3 ml of tetrahydrofuran. 1 ml of tetrahydrofuran solution of 0.14 g of 2-ethylpiperidine was added dropwise at room temperature therein slowly, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 1 ml of tetrahydrofuran solution of 0.2 g of 4,6-dichloro-5-fluoropyrimidine at room temperature, and stirred for 4 hours. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.22 g of 4-chloro-6-(2-ethylpiperidino)-5-fluoropyrimidine.

Workup

  1. stirringstirred for 4 hours
  2. extractionthe mixture was extracted with tert-butyl methyl ether three times
  3. washThe organic layers were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-06070ca4325c40d0b0e2298465a0c6df
Source dataset
uspto-grants-2011_07
Patent number
US07973028B2

Reaction notes

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