ChemicalBook CAS DataBase List 2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-[(E)-phenyldiazenyl]pyrimidine-4,6-diamine

2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-[(E)-phenyldiazenyl]pyrimidine-4,6-diamine synthesis

11synthesis methods

Product Name:2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-[(E)-phenyldiazenyl]pyrimidine-4,6-diamine
CAS Number:1350653-29-0
Molecular formula:C23H17F2N9
Molecular Weight:457.44

1350653-28-9
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62-53-3 Synthesis

62-53-3
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109-77-3 Synthesis

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2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-[(E)-phenyldiazenyl]pyrimidine-4,6-diamine

1350653-29-0
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Yield:1350653-29-0 59%

Reaction Conditions:

Stage #1: anilinewith hydrogenchloride;sodium nitrite in water at 0 - 5; for 0.25 h;
Stage #2: malononitrilewith sodium acetate in ethanol;water at 0; for 2 h;
Stage #3: 5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide acetic acidwith triethylamine in N,N-dimethyl-formamide at 85 - 100; for 4 h;

Steps:

29A Example 29A 2-[5-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-[(E)-phenyldiazenyl]pyrimidine-4,6-diamine

Example 29A
2-[5-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-[(E)-phenyldiazenyl]pyrimidine-4,6-diamine
With stirring, 3.85 g (41.34 mmol) of aniline were added to water (40 ml) and conc. hydrochloric acid (7.07 ml), and this mixture was cooled to 0° C. A solution of 2.85 g (41.34 mmol) of sodium nitrite in water (21 ml) was then added dropwise at between 0° C. and 5° C., followed by stirring at 0° C. for 15 min.
Thereafter, at 0° C., a solution of 4.28 g (52.25 mmol) of sodium acetate in water (19 ml) was rapidly added dropwise, and then, with good stirring, a solution of 2.73 g (41.34 mmol) of malononitrile in ethanol (10 ml) was added dropwise.
After 2 h at 0° C., the resulting precipitate was filtered off with suction and washed three times with water (50 ml each time) and with petroleum ether (50 ml).

References:

US2014/148433,2014,A1 Location in patent:Paragraph 0716; 0717; 0718; 0719

6017-21-6 Synthesis