Water → HCID 19898799, compound

HRID 1196489Notes

Reaction equation

HRID 1196489 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=C1)=O.C(N)C.O>O1CCCC1>[CH3:20][NH:22][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

6

Reactant 4

HCID 962WaterHCID 6341EthylamineHCID 682631,1'-CarbonyldiimidazoleHCID 19898801HCID 19898801, compound

Product 1

HCID 19898799HCID 19898799, compoundYield 85.5%

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 3 hours under a nitrogen atmosphere. A solution of monoethylamine in tetrahydrofuran (16 ml; 0.041 mole; 2.59M) was added, and the mixture was stirred at room temperature for one hour. Water (50 ml) was added to dissolve a precipitate that had formed. The solvents were evaporated under reduced pressure, and the residue was triturated in isopropanol to give 2.96 g of solid, mp 211°-213° C. Recrystallization from a mixture of isopropanol and water provided 2.58 g (70%) of product, mp 212°-214° C.

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. dissolutionto dissolve a precipitate that
  3. customhad formed
  4. customThe solvents were evaporated under reduced pressure
  5. customthe residue was triturated in isopropanol

Sources & evidence

ORD record
ord-de9acf09feee4af086e44cc92e3aa857
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

Loading…