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

HRID 2076895Notes

Reaction equation

HRID 2076895 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-aaebd82704d244d2996251c465c52db2
Source dataset
uspto-grants-2011_04
Patent number
US07928110B2

Reaction notes

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