HCID 71746453, compound → 2-[1-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 570547Notes

Reaction equation

HRID 570547 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2[CH2:10][CH2:11][CH2:12][C:8]=2[C:7]([C:13]2[N:14]=[C:15](I)[C:16]3[C:21]([CH3:23])([CH3:22])[C:20](=[O:24])[NH:19][C:17]=3[N:18]=2)=[N:6]1>CN(C=O)C.[Pd]>[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2[CH2:10][CH2:11][CH2:12][C:8]=2[C:7]([C:13]2[N:14]=[CH:15][C:16]3[C:21]([CH3:23])([CH3:22])[C:20](=[O:24])[NH:19][C:17]=3[N:18]=2)=[N:6]1

Participants

4

Reactant 1

HCID 71746453HCID 71746453, compound

Product 1

HCID 717464542-[1-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-oneYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

45 mg (0.08 mmol) of 2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one were dissolved in 5 ml of absolute DMF, 18 mg (0.02 mmol) of 10% palladium on charcoal were added and hydrogenation was effected under standard hydrogen pressure overnight. The reaction mixture was filtered through Celite and concentrated, and the residue was purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 20:80→100:0). 25 mg of the target compound were obtained (80% of theory).

Workup

  1. custompressure overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated
  4. customthe residue was purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 20:80→100:0)

Sources & evidence

ORD record
ord-60a1f00ecfa546fea7854301f060aebc
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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