Hexane → HCID 13670001, compound

HRID 569981Notes

Reaction equation

HRID 569981 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:21]=[C:20]([CH3:22])[C:19]([C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[CH:18][N:17]=2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:28]CCCCC>CN(C)C=O>[CH2:26]([N:25]1[CH:28]=[CH:22][C:20]2[N:21]=[C:16]([N:13]3[CH2:14][CH2:15][N:10]([CH2:3][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:11][CH2:12]3)[N:17]=[CH:18][C:19]=2[C:23]1=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 8058HexaneHCID 24758Sodium hydrideHCID 13784089HCID 13784089, compound

Product 1

HCID 13670001HCID 13670001, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

After washing 240 mg of sodium hydride (60% in oil, 6 mmol) with hexane, it was suspended in 3 ml of N,N-dimethylformamide (DMF). Thereafter, a DMF solution (10 ml) of 1.7 g (5 mmol) of 2-(4-benzylpiperazino)-N-ethyl-4-methylpyrimidine-5-carboxylic acid amide (Referential Example 5) was added and the reactants were reacted at 150° C. for 1.5 hours. After distilling off DMF under reduced pressure, 100 ml of water was added, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with saturated saline and dried with magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to obtain 1.5 g of the intended product as light yellowish crystals (yield: 87%).

Workup

  1. customthe reactants were reacted at 150° C. for 1.5 hours
  2. distillationAfter distilling off DMF under reduced pressure, 100 ml of water
  3. additionwas added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated saline
  6. dry with materialdried with magnesium sulfate, and ethyl acetate
  7. distillationwas distilled off under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-543e5b35e7a34a518e7484bc0862b37f
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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