Sodium hydride → HCID 22346963, compound

HRID 897634Notes

Reaction equation

HRID 897634 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[C:3]=12.[H-].[Na+].[CH3:25][O:26][C:27]([C:29]1[O:30][C:31]([N+]([O-])=O)=[CH:32][CH:33]=1)=[O:28]>CS(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:31]4[O:30][C:29]([C:27]([O:26][CH3:25])=[O:28])=[CH:33][CH:32]=4)=[CH:15][CH:16]=3)[C:3]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 94882Methyl 5-nitro-2-furoateHCID 135841424HCID 135841424, compound

Product 1

HCID 22346963HCID 22346963, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol (0.107 g, 0.362 mmol, 1.0 equiv), DMSO (0.5 mL), sodium hydride (60%, 0.030 g, 0.72 mmol, 2.0 equiv), and methyl-5-nitro-2-furoate (0.062 g, 0.36 mmol, 1.0 equiv) was heated at 90° C. for 3 h. The reaction mixture was allowed to cool to room temperature, poured into ice water (10 mL), and extracted with three portions of CH2Cl2 (50 mL each). The combined organic extracts were washed with 5% aqueous KOH (50 mL) and the organic layer was dried over MgSO4, filtered, and concentrated to afford a red oil which was purified by column chromatography on silica gel (elution with 300 mL of 5% MeOH/CH2Cl2) to afford methyl 5-[4-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenoxy]-2-furoate as a red solid (0.070 g, 0.17 mmol):

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with three portions of CH2Cl2 (50 mL each)
  3. washThe combined organic extracts were washed with 5% aqueous KOH (50 mL)
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a red oil which
  8. customwas purified by column chromatography on silica gel (elution with 300 mL of 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d37b30c099554f2d8ed235477210d40f
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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