Dimethylamine → HCID 19898817, compound

HRID 1196496Notes

Reaction equation

HRID 1196496 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]([CH2:12][C:13](O)=[O:14])=[C:4]2[N:3]=1.[C:22](N1C=CN=C1)([N:24]1C=CN=[CH:25]1)=O.CNC>O1CCCC1>[CH3:22][N:24]([CH3:25])[C:13](=[O:14])[CH2:12][C:11]1[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:9][N:5]2[C:6]([CH3:8])=[CH:7][C:2]([CH3:1])=[N:3][C:4]=12

Participants

5

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 19898805HCID 19898805, compound

Product 1

HCID 19898817HCID 19898817, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 3.0 g (0.011 mole) of 5,7-dimethyl-2-phenylpyrazolo[1,5-a]pyrimidine-3-acetic acid and 1.73 g (0.011 mole) of 1,1'-carbonyldiimidazole in 120 ml of anhydrous tetrahydrofuran was stirred for 4 hours at room temperature while a stream of nitrogen was bubbled through the mixture. The solution was treated with a solution of dimethylamine in tetrahydrofuran (11.2 ml; 0.033 mole; 2.95M) and the mixture was stirred at room temperature for 17 hours under nitrogen. The solvent was evaporated under reduced pressure, and the residue was dissolved in dichloromethane, extracted with aqueous 7% sodium bicarbonate, and with water, dried over magnesium sulfate and evaporated under reduced pressure (4.5 g). The residue was recrystallized from isopropanol to give 2.1 g (62%) of product, mp 171°-172° C.

Workup

  1. customwas bubbled through the mixture
  2. stirringthe mixture was stirred at room temperature for 17 hours under nitrogen
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane
  5. extractionextracted with aqueous 7% sodium bicarbonate
  6. dry with materialwith water, dried over magnesium sulfate
  7. customevaporated under reduced pressure (4.5 g)
  8. customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-f4924095dc0f44f1bdbb00529ab85cf1
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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