HCID 58938568, compound → HCID 58938683, compound

HRID 598188Notes

Reaction equation

HRID 598188 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22](=[O:24])[N:21]([CH3:25])[C:20]([N:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])=[N:19][C:18]=3[N:17]([CH3:33])[CH:16]=2)=[C:11]([F:34])[CH:10]=1)C1C=CC=CC=1>[Pd]>[CH2:30]([N:26]([CH2:27][CH2:28][CH3:29])[C:20]1[N:21]([CH3:25])[C:22](=[O:24])[C:23]2[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]=3[F:34])=[CH:16][N:17]([CH3:33])[C:18]=2[N:19]=1)[CH2:31][CH3:32]

Participants

3

Reactant 1

HCID 58938568HCID 58938568, compound

Product 1

HCID 58938683HCID 58938683, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 5-[4-(benzyloxy)-2-fluorophenyl]-2-(dipropylamino)-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (194 mg, 0.419 mmol) was added 10% palladium on carbon (50 mg), and the mixture was stirred at room temperature for 15 hours under hydrogen atmosphere. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 25% hexane/ethyl acetate mixture. The desired fractions were concentrated in vacuo, and the resulting crystals were washed with diethyl ether to give 42 mg (27%) of the title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with a 25% hexane/ethyl acetate mixture
  5. concentrationThe desired fractions were concentrated in vacuo
  6. washthe resulting crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-27fd775d04084e70a881080367f93ec7
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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