4,4-Dimethoxy-2-butanone → HCID 68659001, compound

HRID 2264308Notes

Reaction equation

HRID 2264308 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]2[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:3]=12.CC[O-].[Na+].CO[CH:23](OC)[CH2:24][C:25](=O)[CH3:26]>C(O)C>[CH3:26][C:25]1[CH:24]=[CH:23][N:6]2[N:5]=[C:4]3[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:3]3=[C:2]2[N:1]=1.[CH3:26][C:25]1[N:6]2[N:5]=[C:4]3[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:3]3=[C:2]2[N:1]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 2285484,4-Dimethoxy-2-butanoneHCID 2723922Sodium ethoxideHCID 178451527HCID 178451527, compound

Product 2

HCID 68659001HCID 68659001, compoundHCID 68659046HCID 68659046, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 448 mg (2 mmol) of the product from Step A and 80 □L (1 mmol) of NaOEt (21 wt % in ethanol), in 10 mL of anhydrous ethanol, was added 297 □L (2.4 mmol) of 4,4-dimethoxy-2-butanone. The reaction mixture was stirred at ambient temperature for 10 min, then refluxed for 16 h. The mixture was cooled to ambient temperature and the solvent evaporated in vacuo to afford the title compound as an 8:1 mixture with tert-butyl 4-methyl-7H-pyrrolo[3′,4′:3,4]pyrazolo[1,5-a]pyrimidine-8(9H)-carboxylate and was used without purification. LC/MS 275.2 (M+1).

Workup

  1. temperaturerefluxed for 16 h
  2. temperatureThe mixture was cooled to ambient temperature
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-aa2ef48eca134096a52e3f0a2df1a523
Source dataset
uspto-grants-2010_12
Patent number
US07855206B2

Reaction notes

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