Triethylamine → 1-Methyl-5-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1958322Notes

Reaction equation

HRID 1958322 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:14])[C:10]=1[C:11](Cl)=[O:12])=[O:5])[CH3:2].[C:15]1([C:21]2[N:22]=[C:23]3[N:28]=[C:27]([NH2:29])[CH:26]=[CH:25][N:24]3[CH:30]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:14])[C:10]=1[C:11](=[O:12])[NH:29][C:27]1[CH:26]=[CH:25][N:24]2[CH:30]=[C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:22]=[C:23]2[N:28]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amineHCID 60136485Ethyl 5-(chlorocarbonyl)-1-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 673883431-Methyl-5-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Chlorocarbonyl-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (3.60 g, assumed purity 60%, 10 mmol) was added slowly to a cooled (0° C.) solution of 2-phenylimidazo[1,2-a]pyrimidin-7-amine (example 1, step 1, 2.52 g, 12 mmol) and triethylamine (2.02 g, 20 mmol) in dichloromethane (50 ml), and the suspension was stirred overnight at RT. The mixture was taken up in dichloromethane, and washed with water. The combined organic layers were dried (Na2SO4), filtered, and the solvent was evaporated under reduced pressure. The title compound (2.75 g, 71%) was isolated from the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40). MS (m/e)=391.2 [M+H+].

Workup

  1. washwashed with water
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-96088bcb9b5d48c191e6ed6b93fb9392
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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