Dimethylamine → HCID 19898810, compound

HRID 1196494Notes

Reaction equation

HRID 1196494 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([CH2:17][C:18]([OH:20])=O)=[C:11]3[N:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:21](N1C=CN=C1)([N:23]1C=CN=[CH:24]1)=O.CNC>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]([CH2:17][C:18]([N:23]([CH3:24])[CH3:21])=[O:20])=[C:11]3[N:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 19898796HCID 19898796, compound

Product 1

HCID 19898810HCID 19898810, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4.0 g (0.013 mole) of 2-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidine-3-acetic acid and 2.25 g (0.013 mole) of 1,1'carbonyldiimidazole in 150 ml of anhydrous tetrahydrofuran was stirred for 4 hours while a stream of nitrogen was bubbled through the mixture. A solution of dimethylamine in tetrahydrofuran (14.1 ml; 0.0417 mole; 2.59M) was added, and the reaction was stirred for 17 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure and the residue was dissolved in dichloromethane, washed with water, aqueous 7% sodium bicarbonate, and water, and dried over magnesium sulfate and re-evaporated under reduced pressure. The crystalline residue (4.0 g) was recrystallized from isopropanol to give 3.4 g (79%) of product, mp 174°-175.5° C.

Workup

  1. customwas bubbled through the mixture
  2. stirringthe reaction was stirred for 17 hours under nitrogen atmosphere
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with water, aqueous 7% sodium bicarbonate, and water
  6. dry with materialdried over magnesium sulfate
  7. customre-evaporated under reduced pressure
  8. customThe crystalline residue (4.0 g) was recrystallized from isopropanol

Sources & evidence

ORD record
ord-d9d1e106ec1a469d91ad5ed7253d5dc8
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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