Triethylamine → N-(2-morpholinophenyl)methyl 2-phenyl-pyrazolo-[1,5-a]-pyrimidine-5-amide

HRID 1443846Notes

Reaction equation

HRID 1443846 reaction equation
[C:1]1([C:7]2[CH:18]=[C:10]3[N:11]=[C:12]([C:15]([OH:17])=O)[CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[O:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=2[CH2:34][NH2:35])[CH2:28][CH2:27]1>O1CCCC1.C(Cl)(=O)OCC>[O:26]1[CH2:27][CH2:28][N:29]([C:32]2[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=2[CH2:34][NH:35][C:15]([C:12]2[CH:13]=[CH:14][N:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:18]=[C:10]3[N:11]=2)=[O:17])[CH2:30][CH2:31]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2776563(2-(Morpholin-4-yl)phenyl)methanamineHCID 586283942-Phenyl-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid

Product 1

HCID 10387041N-(2-morpholinophenyl)methyl 2-phenyl-pyrazolo-[1,5-a]-pyrimidine-5-amideYield 69%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 10928Ethyl chloroformateSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 2-phenyl- pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid (120 mg), and triethylamine (0.091 ml) in tetrahydrofuran (10 ml), ethyl chlorocarbonate (0.053 ml) was added at −40° C. It was further added with a solution of 2-morpholinobenzylamine (115 mg) in tetrahydrofuran (2 ml), and thereafter heated to −20° C. The reaction solution was distilled under a reduced pressure, and then water was added thereto, extracted with chloroform, and the organic layer was dried with magnesium sulfate. After the reduced-pressure distillation of the solvent, the residue was purified by a silica gel column chromatography, and thereafter recrystallized from acetone-diisopropyl ether to yield N-(2-morpholinophenyl)methyl 2-phenyl-pyrazolo-[1,5-a]-pyrimidine-5-amide (142 mg, 69%). mp: 190-192° C.

Workup

  1. distillationThe reaction solution was distilled under a reduced pressure
  2. additionwater was added
  3. extractionextracted with chloroform
  4. dry with materialthe organic layer was dried with magnesium sulfate
  5. distillationAfter the reduced-pressure distillation of the solvent
  6. customthe residue was purified by a silica gel column chromatography
  7. customrecrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-896e37068eff45ccbfea02885e1ba311
Source dataset
uspto-grants-2010_02
Patent number
US07662826B2

Reaction notes

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