Pyrazolidine → 2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 7638Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][NH:2]1.C[O:7][C:8](=O)[CH:9]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:10]([C:12]1[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=1)=O>N1C=CC=CC=1>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:9]2[C:8](=[O:7])[N:2]3[CH2:3][CH2:4][CH2:5][N:1]3[C:10]=2[C:12]2[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of pyrazolidine (7.8 g, 54.16 mmol) in pyridine (100 mL) is added 2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-propionic acid methyl ester, 3, (11.5 g, 36.1 mmol). The reaction mixture is heated to 90° C. for 16 hours. The solvent is removed in vacuo and the resulting residue purified over silica (100% EtOAc, followed by 10% MeOH/EtOAc) to afford 3.9 g (37% yield) of the desired product as a yellow solid.

Workup

customThe solvent is removed in vacuo
customthe resulting residue purified over silica (100% EtOAc, followed by 10% MeOH/EtOAc)

Sources & evidence

ORD record: ord-ac24702ae6f64a9aaf0f876ca8221ebb
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087615B2

Reaction notes

Loading…