Ammonium Hydroxide → 4-Amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxamide

HRID 510073Notes

Reaction equation

HRID 510073 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:3]=1.O[N:29]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[OH-].[NH4+]>CN(C=O)C.C(#N)C.O>[NH2:1][C:2]1[C:7]([C:8]([NH2:29])=[O:10])=[CH:6][N:5]=[C:4]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:3]=1

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66614346HCID 66614346, compound

Product 1

HCID 98853504-Amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

300 mg (0.82 mmol) of 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxylic acid (example 102A) and 139 mg (0.91 mmol) of 1-hydroxyl-1H-benzotriazole were dissolved in 2.2 ml of DMF, and 174 mg (0.91 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added. While cooling with ice, 140 ml (0.99 mmol) of ammonium hydroxide (28%) were added, and the mixture was reacted at room temperature overnight. 4 ml of acetonitrile/water (1/1) were added and the precipitate formed was filtered off. After drying under high vacuum, 145 mg (48% of theory) of the target compound were obtained.

Workup

  1. additionwere added
  2. customthe mixture was reacted at room temperature overnight
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. customAfter drying under high vacuum, 145 mg (48% of theory) of the target compound
  6. customwere obtained

Sources & evidence

ORD record
ord-ce41818563704610b85b1938467ca82f
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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