Ammonia → 3-[1-(2-Fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-7,7-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-e][1,2,4]triazin-6-one

HRID 570551Notes

Reaction equation

HRID 570551 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15]2[N:16]=[N:17][C:18]([C:22]([CH3:28])([CH3:27])[C:23](OC)=[O:24])=[C:19](O)[N:20]=2)=[N:6]1.P(Cl)(Cl)(Cl)=O.[NH3:38]>C(#N)C>[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15]2[N:16]=[N:17][C:18]3[C:22]([CH3:27])([CH3:28])[C:23](=[O:24])[NH:38][C:19]=3[N:20]=2)=[N:6]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178500127HCID 178500127, compound

Product 1

HCID 717466383-[1-(2-Fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-7,7-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-e][1,2,4]triazin-6-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

182 mg (0.42 mmol) of methyl 2-{3-[1-(2-fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-5-hydroxy-1,2,4-triazin-6-yl}-2-methylpropanoate were admixed with 3.8 ml (40.87 mmol) of phosphoryl chloride and the mixture was stirred at RT for 2.5 h. The reaction solution was diluted with 20 ml of dry acetonitrile and gradually added dropwise while cooling with ice to 40 ml of a 25% aqueous ammonia solution, and the mixture was stirred at RT for 2 h. The reaction mixture was concentrated on a rotary evaporator and the precipitate was filtered off. The residue was stirred with DMF/methanol and filtered with suction, and the solids were dried under high vacuum. 98 mg of the target compound were obtained (purity 92%; 53% of theory).

Workup

  1. additiongradually added dropwise
  2. stirringthe mixture was stirred at RT for 2 h
  3. concentrationThe reaction mixture was concentrated on a rotary evaporator
  4. filtrationthe precipitate was filtered off
  5. stirringThe residue was stirred with DMF/methanol
  6. filtrationfiltered with suction
  7. customthe solids were dried under high vacuum

Sources & evidence

ORD record
ord-89e2e6fd060f44aa8596067556f3c0d4
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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