Sodium Carbonate → 5-amino-1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 403492Notes

Reaction equation

HRID 403492 reaction equation
[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2].[C:23](/[C:25](=[CH:31]\OCC)/[C:26]([O:28][CH2:29][CH3:30])=[O:27])#[N:24].[C:35]([O-])(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.CC(O)=O>[CH2:29]([O:28][C:26]([C:25]1[C:31]([CH3:35])=[N:22][N:21]([C:18]2[CH:17]=[CH:16][C:15]([CH2:14][C:13]3[C:3]([CH2:1][CH3:2])=[N:4][N:5]4[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][C:6]=34)=[CH:20][CH:19]=2)[C:23]=1[NH2:24])=[O:27])[CH3:30]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 517045Sodium AcetateHCID 1715183Ethyl 2-cyano-3-ethoxyacrylateHCID 68390855[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-hydrazine

Product 1

HCID 683789025-amino-1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-hydrazine (15) (1.8 g, 6.1 mmol) was dissolved in 40 ml water/AcOH (1:3), and after addition of (E)-ethyl 2-cyano-3-ethoxyacrylate (1.24 g, 7.3 mmol) and sodium acetate (1.1 g, 13.4 mmol) the reaction mixture was stirred for 3 h at 100° C. Sodium carbonate was added (pH 11). The organic layer was extracted 2 times with EtOAc, washed with water and brine, dried over Na2 SO4 and concentrated. The crude product was purified by chromatography (50-90% EtOAc in cyclohexane).

Workup

  1. extractionThe organic layer was extracted 2 times with EtOAc
  2. washwashed with water and brine
  3. customdried over Na2 SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography (50-90% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-ad01dd635f394af2a9802adacba023f3
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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