Tetrahydrofuran → HCID 69596297, compound

HRID 2417372Notes

Reaction equation

HRID 2417372 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:10])[CH3:9].O1CCCC1.[H-].[Na+].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[N:36]=[C:35](Cl)[CH:34]=[CH:33][N:32]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>O>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[N:32]=[C:33]([O:10][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH3:9])[CH:34]=[CH:35][N:36]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 260821-(2-Chlorophenyl)ethanolHCID 46738270tert-Butyl 4-(4-chloropyrimidin-2-yl)piperazine-1-carboxylate

Product 1

HCID 69596297HCID 69596297, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2-Chloro-phenyl)-ethanol (31.4 mg, 0.20 mmol) was dissolved into 1.7 mL of anhydrous tetrahydrofuran and treated with sodium hydride (8.0 mg, 60% dispersion in mineral oil, 0.20 mmol). This was stirred under nitrogen for 1 hour at ambient temperature, then the reaction was treated with 4-(4-chloro-pyrimidin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (I-2a) (50 mg, 0.17 mmol) in one portion. The resultant mixture was refluxed under nitrogen for 4 hours. After cooling to room temperature, the reaction was poured into water (20 mL) and extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with brine (20 mL), then dried over sodium sulfate, filtered, and concentrated. The residue was purified by preparative TLC (7:13 ethyl acetate:hexanes) to afford 64.3 mg of the title product (I-2b).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. washThe combined organic extracts were washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC (7:13 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-4e273698acd74690836b33b630ffeb8c
Source dataset
uspto-grants-2004_11
Patent number
US06825198B2

Reaction notes

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