Acetonitrile → HCID 25017125, compound

HRID 524553Notes

Reaction equation

HRID 524553 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][NH:14]3)=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]=2)[N:3]=1.Br[CH2:25][CH2:26][O:27][CH3:28].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[CH2:25][CH2:26][O:27][CH3:28])=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 178426370HCID 178426370, compound

Product 1

HCID 25017125HCID 25017125, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

[2-(3,5-Dimethyl-pyrazol-1-yl)-9H-purin-6-yl]-phenyl-amine (300 mg, 0.88 mmol), 2-bromoethylmethylether (0.12 mL, 1.32 mmol), potassium carbonate (121 mg, 0.88 mmol) and acetonitrile were mixed and heated in a microwave oven at 120° C. for 40 min. Water was added resulting in a white precipitate. The crude product was purified by preparative LCMS to give [2-(3,5-dimethyl-pyrazol-1-yl)-9-(2-methoxy-ethyl)-9H-purin-6-yl]-phenyl-amine (27 mg, 9%) as a white crystalline compound.

Workup

  1. customresulting in a white precipitate
  2. customThe crude product was purified by preparative LCMS

Sources & evidence

ORD record
ord-0fda52ec40dd40bbaf3edef52228e2b5
Source dataset
uspto-grants-2016_05
Patent number
US09340544B2

Reaction notes

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