HCID 86704207, compound → 1-[2-(4,6-Dimethoxy-pyrimidin-2-yloxy)-ethyl]-1H-pyrazol-4-ylamine

HRID 624013Notes

Reaction equation

HRID 624013 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[N:15]2)[N:4]=1>CCOC(C)=O.CCO.O=[Pt]=O>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([NH2:19])[CH:16]=[N:15]2)[N:6]=1

Participants

5

Reactant 1

HCID 86704207HCID 86704207, compound

Product 1

HCID 682827731-[2-(4,6-Dimethoxy-pyrimidin-2-yloxy)-ethyl]-1H-pyrazol-4-ylamine

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,6-dimethoxy-2-(2-(4-nitro-1H-pyrazol-1-yl)ethoxy)pyrimidine (2.05 g, 6.93 mmol), in EtOAc (3.0 mL, degassed) and EtOH (9 mL, degassed), PtO2 (135 mg, 0.70 mmol) was added and the reaction mixture was stirred at rt under a H2-atmosphere for 3 h. The mixture was diluted with EtOH, filtered over celite and the filter cake was rinsed with EtOH. The filtrate was concentrated to obtain the title compound as a red oil. LC-MS conditions A: tR=0.58 min, [M+H]+=266.02.

Workup

  1. filtrationfiltered over celite
  2. washthe filter cake was rinsed with EtOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1c04a8914b4b45e5958600a82c0491af
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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