Dimethylformamide → 3,5-Dimethyl-1-(6-methylergolin-8beta-ylmethyl)pyrazole

HRID 986527Notes

Reaction equation

HRID 986527 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH:8]=[CH:7][C:6]([CH3:9])=[N:5]1.S(C1C=CC(C)=CC=1)(OC[C@@H:15]1[CH2:29][C@H:28]2[C@@H:18]([CH2:19][C:20]3[C:30]4[C:23](=[CH:24][CH:25]=[CH:26][C:27]2=4)[NH:22][CH:21]=3)[N:17]([CH3:31])[CH2:16]1)(=O)=O.[CH3:39]N(C)C=O>>[CH3:9][C:6]1[CH:7]=[C:8]([CH3:39])[N:4]([CH2:3][C@@H:15]2[CH2:29][C@H:28]3[C@@H:18]([CH2:19][C:20]4[C:30]5[C:23](=[CH:24][CH:25]=[CH:26][C:27]3=5)[NH:22][CH:21]=4)[N:17]([CH3:31])[CH2:16]2)[N:5]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 790961H-Pyrazole, 1,3-dimethyl-HCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Product 1

HCID 103595383,5-Dimethyl-1-(6-methylergolin-8beta-ylmethyl)pyrazole

Procedure

0.7 g of 50% sodium hydride in an oil was added in small portions to a mixture of 1.9 g of 2,5-dimethylpyrazole and 50 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 3 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluted with ethyl acetate:ethanol=10:1 by volume). The product was recrystallized from isopropyl alcohol to obtain 0.8 g of the titled compound as colorless prisms having a melting point of 187°-190° C.

Workup

  1. temperaturewas then heated on a water bath for 3 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate:ethanol=10:1 by volume)
  4. customThe product was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-14d271d2cbf947d5a395ade9445e376b
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

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