Ammonia → 3-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-isopropyl-1,2,4-triazine-5-amine

HRID 2278865Notes

Reaction equation

HRID 2278865 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[N:16][C:17]([CH:21]([CH3:23])[CH3:22])=[C:18](O)[N:19]=2)=[N:6]1.P(Cl)(Cl)(Cl)=O.[NH3:33]>C(#N)C>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[N:16][C:17]([CH:21]([CH3:23])[CH3:22])=[C:18]([NH2:33])[N:19]=2)=[N:6]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178440333HCID 178440333, compound

Product 1

HCID 716219833-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-isopropyl-1,2,4-triazine-5-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

900 mg (5.138 mmol) of 3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-isopropyl-1,2,4-triazin-5-ol were admixed with 12 ml of phosphoryl chloride and stirred overnight at RT. The reaction mixture was diluted with 50 ml of dry acetonitrile and, with ice-cooling, stirred into 173 ml of concentrated aqueous ammonia solution (25% strength). The reaction mixture was stirred for 2 h at RT and for 6 h at 50° C. After cooling, concentration on a rotary evaporator was carried out.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred for 2 h at RT and for 6 h at 50° C
  3. temperatureAfter cooling
  4. concentrationconcentration
  5. customon a rotary evaporator

Sources & evidence

ORD record
ord-18771e18e4b1463ba1675b24e11088b1
Source dataset
uspto-grants-2015_09
Patent number
US09133191B2

Reaction notes

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