2-[3-(2-Fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-5-nitropyrimidine-4,6-diamine → HCID 24794429, compound

HRID 1875456Notes

Reaction equation

HRID 1875456 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[N:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([N+:21]([O-])=O)=[C:16]([NH2:24])[N:15]=2)[N:6]=1>N1C=CC=CC=1.[Pd]>[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[N:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[C:16]([NH2:24])[N:15]=2)[N:6]=1

Participants

4

Reactant 1

HCID 591778732-[3-(2-Fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-5-nitropyrimidine-4,6-diamine

Product 1

HCID 24794429HCID 24794429, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

690 mg (1.42 mmol) of 2-[3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-5-nitropyrimidine-4,6-diamine from example 15A are dissolved in 120 ml of pyridine. 270 mg of 10% palladium on activated carbon are added, and hydrogenation is carried out under a hydrogen pressure of 3.5 bar for 15 h. The catalyst is then filtered off and washed with ethanol. The residue after concentration to dryness is stirred with ethanol at 50° C. and filtered off with suction. 378 mg (76% of theory) of the desired product are obtained. A further 92 mg (18% of theory) of the target compound can be obtained from the filtrate by purifying by preparative HPLC.

Workup

  1. customfor 15 h
  2. filtrationThe catalyst is then filtered off
  3. washwashed with ethanol
  4. concentrationThe residue after concentration to dryness
  5. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-5a0310e471ef47098f6ad1a28482e1bf
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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