N,N-dimethylformamide ethanol → HCID 178469879, compound

HRID 1038780Notes

Reaction equation

HRID 1038780 reaction equation
[NH:1]1[C:5]([NH:6][CH:7]=[C:8]([C:12]([O-:14])=O)[C:9]([O-:11])=[O:10])=[CH:4][CH:3]=[N:2]1.CN(C=O)C.[CH3:20][CH2:21]O>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[O:14]=[C:12]1[N:1]2[N:2]=[CH:3][CH:4]=[C:5]2[NH:6][CH:7]=[C:8]1[C:9]([O:11][CH2:20][CH3:21])=[O:10]

Participants

4

Reactant 2

HCID 19794673N,N-dimethylformamide ethanolHCID 86649657HCID 86649657, compound

Product 1

HCID 178469879HCID 178469879, compound

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

A solution of the 2-((1H-pyrazol-5-ylamino)methylene)malonate (4.0 g, 15.8 mmol) in Dowtherm (15 mL) was heated to 250° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, DMF/EtOH (10 mL, 1/1, v/v) was added to the mixture and formed precipitate was filtered, which was washed with EtOH and dried under vacuum to give ethyl 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate; 1.9 g (58%). 1H NMR (300 MHz, DMSO) δ 13.01 (brs, 1H), 8.58 (s, 1H), 7.91 (d, J=2.1 Hz, 1H), 6.30 (d, J=1.8 Hz, 1H), 4.22 (q, J=7.2 Hz, 2H), 1.27 (t, J=7.2 Hz, 3H).

Workup

  1. customformed precipitate
  2. filtrationwas filtered
  3. washwhich was washed with EtOH
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4e223f1da2b145beb95df3c854a448ba
Source dataset
uspto-grants-2013_10
Patent number
US08552006B2

Reaction notes

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