Ethyl cyanoacetate → HCID 49788129, compound

HRID 1968549Notes

Reaction equation

HRID 1968549 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[Na].[NH2:10][C:11]1[N:16]=[C:15]([C:17](=[O:20])[CH2:18]Br)[CH:14]=[CH:13][N:12]=1.C(N(C(C)C)CC)(C)C>CCO.C1COCC1>[CH2:1]([O:3][C:4](=[O:8])[CH:5]([C:6]#[N:7])[CH2:18][C:17]([C:15]1[CH:14]=[CH:13][N:12]=[C:11]([NH2:10])[N:16]=1)=[O:20])[CH3:2]

Participants

7

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 81531DiisopropylethylamineHCID 5360545Sodium2×HCID 116009641-(2-aminopyrimidin-4-yl)-2-bromoethanone

Product 1

HCID 49788129HCID 49788129, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethylcyanoacetate (5.3 mL, 0.05 mol) was added to a suspension of sodium metal (1.15 g, 0.05 mol) in 150 mL of anhydrous EtOH at 0° C. After sodium dissolution the reaction mixture was concentrated and the resultant solid was added to a solution of 1-(2-amino-pyrimidin-4-yl)-2-bromo-ethanone (15 g, 0.05 mol) in 300 mL of anhydrous THF and diisopropylethylamine (8.8 mL, 0.05 mol). The reaction mixture was stirred overnight at rt, concentrated and the residue was suspended in water and extracted with DCM. The organic extracts were dried (Na2SO4) and concentrated. The crude was purified by flash chromatography (DCM/MeOH 95:5) to give 4.5 g (37%) of the title compound as an oil.

Workup

  1. concentrationwas concentrated
  2. concentrationconcentrated
  3. extractionextracted with DCM
  4. dry with materialThe organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude was purified by flash chromatography (DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-955a8b5efadd43a6b25542e9dbc6a55f
Source dataset
uspto-grants-2013_04
Patent number
US08426417B2

Reaction notes

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