2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → HCID 59173386, compound

HRID 220089Notes

Reaction equation

HRID 220089 reaction equation
[C:1]([O:5][C:6](=[O:17])[N:7]([C:9]1[CH:14]=[C:13]([NH:15][NH2:16])[N:12]=[CH:11][N:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([O:20][C:21](=[O:29])[C:22]([C:27]#[N:28])=[CH:23]OCC)[CH3:19]>C(O)C>[CH2:18]([O:20][C:21]([C:22]1[CH:23]=[N:16][N:15]([C:13]2[CH:14]=[C:9]([N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:17])[CH3:8])[N:10]=[CH:11][N:12]=2)[C:27]=1[NH2:28])=[O:29])[CH3:19]

Participants

4

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 59173582HCID 59173582, compound

Product 1

HCID 59173386HCID 59173386, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (6-hydrazino-pyrimidin-4-yl)-methyl-carbamic acid tert-butyl ester (4.0 g, 16.7 mmol), 2-cyano-3-ethoxy-acrylic acid ethyl ester (3.02 g, 17.5 mmol) and ethanol (25 mL) is heated to reflux for 4 hours. The reaction mixture is then concentrated and triturated with water (10 mL). White precipitate forms. After filtration, the undissolved solid is further washed with water, then air-dried to give 5-amino-1-[6-(tert-butoxycarbonyl-methyl-amino)-pyrimidin-4-yl]-1H-pyrazole-4-carboxylic acid ethyl ester as white powder.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture is then concentrated
  4. customtriturated with water (10 mL)
  5. filtrationAfter filtration
  6. washthe undissolved solid is further washed with water
  7. customair-dried

Sources & evidence

ORD record
ord-3fdc780a8700411696fdfa973321b1fb
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Reaction notes

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