Iodine → 2-(biphenyl-4-ylmethyl)-3-iodo-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81412Notes

Reaction equation

HRID 81412 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([N:11]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:12](=[O:19])[N:13]([CH3:18])[C:14]3=[O:17])=[N:9]2)=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.[I:38]I>C1COCC1>[C:1]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[C:16]([I:38])=[C:15]3[C:10]([N:11]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:12](=[O:19])[N:13]([CH3:18])[C:14]3=[O:17])=[N:9]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 685054602-(Biphenyl-4-ylmethyl)-7-isobutyl-5-methyl-2h-pyrazolo[3,4-d]pyrimidine-4,6(5h,7h)-dione

Product 1

HCID 685050642-(biphenyl-4-ylmethyl)-3-iodo-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

2-(biphenyl-4-ylmethyl)-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (203 mg, 0.523 mmol) is dissolved in anhydrous THF (5 mL), and then cooled to −78° C. 1.8 M solution of LDA in THF (600 uL) is added dropwise with rigorous stirring at −78° C., followed by the addition of iodine (160 mg, 0.63 mmol) in THF. The reaction mixture is stirred at −78° C. for an hour, and then is allowed to warm up to room temperature before quenching. The mixture is poured into saturated NH4Cl solution, and then extracted with ethyl acetate three times. The combined organic phase is washed with potassium iodide aqueous solution (1 M), water, and then dried over Na2SO4. Solvent is removed under reduced vacuum to give crude product was white solids. MS (ESI) m/z 515.1 [M+H]+.

Workup

  1. stirringThe reaction mixture is stirred at −78° C. for an hour
  2. temperatureto warm up to room temperature
  3. custombefore quenching
  4. additionThe mixture is poured into saturated NH4Cl solution
  5. extractionextracted with ethyl acetate three times
  6. washThe combined organic phase is washed with potassium iodide aqueous solution (1 M), water
  7. dry with materialdried over Na2SO4
  8. customSolvent is removed under reduced vacuum
  9. customto give crude product

Sources & evidence

ORD record
ord-015f38ef5d244268a62e8df886a6a395
Source dataset
uspto-grants-2014_09
Patent number
US08846693B2

Reaction notes

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