Potassium Carbonate → 8-{1-[3-(4-Fluoro-phenyl)-prop-2-ynyl]-1H-pyrazol-4-yl}-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

HRID 536007Notes

Reaction equation

[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([C:22]3[CH:23]=[N:24][NH:25][CH:26]=3)=[N:8][C:7]=2[N:6]=[C:5]1[N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]#[C:41][C:42]1[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=1>CC(C)=O>[F:48][C:45]1[CH:46]=[CH:47][C:42]([C:41]#[C:40][CH2:39][N:24]2[CH:23]=[C:22]([C:9]3[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:11]4[C:12](=[O:13])[N:4]([CH2:1][CH2:2][CH3:3])[C:5]([N:27]5[CH2:28][CH2:29][CH2:30][CH2:31]5)=[N:6][C:7]=4[N:8]=3)[CH:26]=[N:25]2)=[CH:43][CH:44]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-Propyl-8-(1H-pyrazol-4-yl)-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.111 g, 0.25 mmol), potassium carbonate (0.052 g, 0.38 mmol), 1-(3-bromo-prop-1-ynyl)-4-fluoro-benzene (0.69 g, 0.33 mmol) was taken in acetone (10 ml). The reaction mixture was heated at 80° C. for 2 hours. The mixture was cooled to room temperature and filtered through sintered funnel, washed with acetone. Solvent was evaporated and the residue was purified by preparative TLC to obtain pure 8-{1-[3-(4-Fluoro-phenyl)-prop-2-ynyl]-1H-pyrazol-4-yl}-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.025 g, 22%) as colourless oil.

Workup

temperatureThe mixture was cooled to room temperature
filtrationfiltered through sintered funnel
washwashed with acetone
customSolvent was evaporated
customthe residue was purified by preparative TLC

Sources & evidence

ORD record: ord-d50b9b642f5344c2a7810090108f4661
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859566B2

Reaction notes

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