Water → HCID 9925691, compound

HRID 1602877Notes

Reaction equation

HRID 1602877 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.[CH2:11]([C:15]1[CH:20]=[C:19](Cl)[N:18]2[N:22]=[CH:23][CH:24]=[C:17]2[N:16]=1)[CH2:12][CH:13]=[CH2:14].O>CN(C=O)C>[CH2:11]([C:15]1[CH:20]=[C:19]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=2)[N:18]2[N:22]=[CH:23][CH:24]=[C:17]2[N:16]=1)[CH2:12][CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 962WaterHCID 114724-HydroxymethylpyridineHCID 24758Sodium hydrideHCID 15462308HCID 15462308, compound

Product 1

HCID 9925691HCID 9925691, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

60% sodium hydride, 0.55 g, was added to a 10 ml-solution of 1.6 g of 4-(hydroxymethyl)pyridine in DMF while being ice-cooled. After the mixture was stirred at 0° C. for 30 minutes, a DMF solution (2.5 ml) containing 2.6 g of 5-(3-butenyl)-7-chloropyrazolo[1,5-a]pyrimidine was added dropwise while being ice-cooled. The mixture was stirred at the same temperature for another 1 hour. After completion of the reaction, water was added to the reaction mixture. The crystals precipitated were collected by filtration and washed with water and then with diethyl ether. The crude crystals obtained were recrystallized from ethyl acetate-n-hexane to provide 1.5 g of the title compound as colorless crystals. The structure and melting point of the compound obtained are shown in Table 1.

Workup

  1. temperaturecooled
  2. additionwas added dropwise
  3. temperaturecooled
  4. stirringThe mixture was stirred at the same temperature for another 1 hour
  5. additionwas added to the reaction mixture
  6. customThe crystals precipitated
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customThe crude crystals obtained
  10. customwere recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-4205bc1e009f4dff926864919b0a9bec
Source dataset
uspto-grants-1999_11
Patent number
US05985882

Reaction notes

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