Dimethylformamide → 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrido[4,3-d]pyrimidin-5(6H)-one

HRID 510102Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

Under argon, 21 mg (0.522 mmol) of sodium hydride (60% suspension in mineral oil) were initially charged and washed repeatedly with hexane. Subsequently, dimethylformamide (0.18 ml) was added, and a solution of 158 mg (0.435 mmol) of the compound from example 46A in dimethylformamide (6.0 ml) was added to the suspension. The reaction mixture was stirred at 150° C. for two days, then diluted with acetonitrile at RT, then filtered, and the filtrate was concentrated. The residue was separated by means of preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient) and the product fractions were concentrated. This gave 31 mg (18% of theory) of the title compound in solid form.

Workup

washwashed repeatedly with hexane
additionSubsequently, dimethylformamide (0.18 ml) was added
filtrationfiltered
concentrationthe filtrate was concentrated
customThe residue was separated by means of preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient)
concentrationthe product fractions were concentrated

Sources & evidence

ORD record: ord-43cc28fdc84e49558fd09520b25f6ce6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

Loading…