Ethyl 5,5,5-trifluoro-2,4-dioxopentanoate → ethyl 1-(2,4-dimethoxypyrimidin-5-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxylate

HRID 873890Notes

Reaction equation

HRID 873890 reaction equation
[NH:1]([C:3]1[C:4]([O:11][CH3:12])=[N:5][C:6]([O:9][CH3:10])=[N:7][CH:8]=1)[NH2:2].[F:13][C:14]([F:26])([F:25])[C:15](=O)[CH2:16][C:17](=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19]>>[CH3:10][O:9][C:6]1[N:5]=[C:4]([O:11][CH3:12])[C:3]([N:1]2[C:15]([C:14]([F:13])([F:25])[F:26])=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:2]2)=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 19576760Ethyl 5,5,5-trifluoro-2,4-dioxopentanoateHCID 896024745-Hydrazinyl-2,4-dimethoxypyrimidine

Product 1

HCID 117703135ethyl 1-(2,4-dimethoxypyrimidin-5-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxylate

Procedure

The title compound was prepared in analogy to the procedure described in Step 17.3 using 5-hydrazinyl-2,4-dimethoxypyrimidine (Step 46.8) and ethyl 5,5,5-trifluoro-2,4-dioxopentanoate at 100° C. for 2 hr. The crude product was purified by silica gel column chromatography (hexane/30% EtOAc). tR: 1.09 min (LC-MS 2); ESI-MS: 347 [M+H]+ (LC-MS 2); Rf=0.31 (hexane/30% EtOAc).

Workup

  1. customThe crude product was purified by silica gel column chromatography (hexane/30% EtOAc)

Sources & evidence

ORD record
ord-0ffcba1a04a04ee38eb59bd0fde717c5
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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