Ethanol → 3-[4-amino-3-(4,5-dihydro-1H-imidazol-2-yl)pyrazolo[3,4-d]pyrimidin-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one

HRID 522328Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:13]3[CH2:17][CH2:16][N:15]([C:18]4[CH:19]=[N:20][N:21]([C:26]5[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=5)[C:22]=4[CH:23]([CH3:25])[CH3:24])[C:14]3=[O:33])[N:9]=[C:10]([C:11]#[N:12])[C:3]=12.CCO.[CH2:37](N)[CH2:38][NH2:39]>CC(O)=O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:13]3[CH2:17][CH2:16][N:15]([C:18]4[CH:19]=[N:20][N:21]([C:26]5[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=5)[C:22]=4[CH:23]([CH3:24])[CH3:25])[C:14]3=[O:33])[N:9]=[C:10]([C:11]3[NH:39][CH2:38][CH2:37][N:12]=3)[C:3]=12

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-amino-1-[1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-d]pyrimidine-3-carbonitrile (0.055 g, 0.12 mmol) in ethane-1,2-diamine (1.5 mL), HOAc (0.23 mL), and EtOH (2.0 mL) was stirred at 100° C. for 45 min. The mixture was then cooled to room temperature, quenched with sat. aq. NaHCO3 (50 mL), and extracted with IPA:CHCl3 (1:2 v/v, 100 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-[4-amino-3-(4,5-dihydro-1H-imidazol-2-yl)pyrazolo[3,4-d]pyrimidin-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.057 g, 97%).

Workup

temperatureThe mixture was then cooled to room temperature
customquenched with sat. aq. NaHCO3 (50 mL)
extractionextracted with IPA:CHCl3 (1:2 v/v, 100 mL)
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b2c0313481c8481085d01c3df4608ea7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328116B2

Reaction notes

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