Diethyl phenylmalonate → Methyl 5,7-dihydroxy-6-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylate

HRID 1915613Notes

Reaction equation

HRID 1915613 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[NH:4][N:3]=1.C([O:13][C:14](=O)[CH:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:16](OCC)=[O:17])C.C(N(C(C)C)CC)(C)C>CN(C=O)C>[OH:13][C:14]1[C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:16]([OH:17])[N:3]2[N:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[CH:6]=[C:2]2[N:1]=1

Participants

5

Reactant 3

HCID 66514Diethyl phenylmalonateHCID 81531DiisopropylethylamineHCID 18445864Methyl 5-amino-1H-pyrazole-3-carboxylate

Product 1

HCID 178497008Methyl 5,7-dihydroxy-6-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.0 g Methyl 3-amino-1H-pyrazole-5-carboxylate, 8.3 ml diethyl-phenylmalonate and 50 ml diisopropylethylamine in 50 ml DMF is heated to 150° C. for 40 h. The solvent is removed, the solid residue is dissolved in 2-propanol the mixture is stirred for 3 hours. The desired product is filtrated, dried and is used without further purification.

Workup

  1. customThe solvent is removed
  2. dissolutionthe solid residue is dissolved in 2-propanol the mixture
  3. filtrationThe desired product is filtrated
  4. customdried
  5. customis used without further purification

Sources & evidence

ORD record
ord-7434097effea46b2b235c323818b7d0d
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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