Dimethylamine → HCID 19898802, compound

HRID 1196488Notes

Reaction equation

HRID 1196488 reaction equation
[C:1]1([C:7]2[C:15]([CH2:16][C:17]([OH:19])=O)=[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](N1C=CN=C1)([N:22]1C=CN=[CH:23]1)=O.CNC>O1CCCC1>[CH3:20][N:22]([CH3:23])[C:17](=[O:19])[CH2:16][C:15]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[N:11][C:10]=12

Participants

5

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 19898801HCID 19898801, compound

Product 1

HCID 19898802HCID 19898802, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3.5 g (0.013 mole) of 2-phenylpyrazolo[1,5-a]pyrimidine-3-acetic acid and 2.24 g (0.013 mole) of 1,1'-carbonyldiimidazole in 150 ml of anhydrous tetrahydrofuran was stirred for 4 hours under a nitrogen atmosphere. A solution of dimethylamine in tetrahydrofuran (14.0 ml of a 2.95M solution; 0.0414 mole) was added. The mixture was stirred at room temperature for one hour. The solvent was evaporated under reduced pressure, and the residue was dissolved in methylene chloride (100 ml). The solution was extracted with 7% aqueous sodium bicarbonate, and with water, and then dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The crystalline residue (4.6 g) was recrystallized from isopropanol to give 2.77 g (72%) of product, mp 156°-157.5° C.

Workup

  1. addition0.0414 mole) was added
  2. stirringThe mixture was stirred at room temperature for one hour
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in methylene chloride (100 ml)
  5. extractionThe solution was extracted with 7% aqueous sodium bicarbonate
  6. dry with materialwith water, and then dried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe crystalline residue (4.6 g) was recrystallized from isopropanol

Sources & evidence

ORD record
ord-a9fa7de99ce44ffabdaf274d810cdd6f
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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