Water → 9-isopropyl-N-(1-methyl-1H-pyrazol-4-yl)-2-(3-nitrophenoxy)-9H-purin-6-amine

HRID 928167Notes

Reaction equation

HRID 928167 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].Cl[C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:23]([CH3:25])[CH3:24])=[C:16]([NH:26][C:27]2[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=2)[N:15]=1.O>CN(C=O)C>[CH:23]([N:20]1[CH:19]=[N:18][C:17]2[C:21]1=[N:22][C:14]([O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[N:15][C:16]=2[NH:26][C:27]1[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=1)([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 111373-NitrophenolHCID 24758Sodium hydrideHCID 118073689HCID 118073689, compound

Product 1

HCID 1180735689-isopropyl-N-(1-methyl-1H-pyrazol-4-yl)-2-(3-nitrophenoxy)-9H-purin-6-amineYield 18.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-nitro-phenol (143 mg, 1.03 mmol) in DMF (15 mL) was added sodium hydride (56 mg, 1.4 mmol) slowly and the mixture was stirred at rt for 30 min. 2-chloro-9-isopropyl-N-(1-methyl-1H-pyrazol-4-yl)-9H-purin-6-amine (200 mg, 0.69 mmol), as prepared in step 1 of Example 2, was added slowly. After the addition, the mixture was stirred at 110° C. overnight. The cooled reaction mixture was poured into water (100 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were dried over Na2SO4, concentrated and the residue was purified by flash column chromatography (MeOH:EtOAc=1:10) to give the title compound (50 mg, 18% yield) as light yellow oil.

Workup

  1. additionwas added slowly
  2. additionAfter the addition
  3. stirringthe mixture was stirred at 110° C. overnight
  4. customThe cooled reaction mixture
  5. extractionextracted with EtOAc (2×30 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. concentrationconcentrated
  8. customthe residue was purified by flash column chromatography (MeOH:EtOAc=1:10)

Sources & evidence

ORD record
ord-4d8f64627612412a938a1da1bfc0eb63
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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