Hydrochloric Acid → Hydrochloric Acid

HRID 2424767Notes

Reaction equation

HRID 2424767 reaction equation
C([N:8]1[CH2:12][C@@H:11]([CH3:13])[C@H:10]([C:14]2[NH:15][C:16](=[O:28])[C:17]3[CH:22]=[N:21][N:20]([CH:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[C:18]=3[N:19]=2)[CH2:9]1)C1C=CC=CC=1.[ClH:29]>C(O)C.[OH-].[Pd+2].[OH-]>[CH:23]1([N:20]2[C:18]3[N:19]=[C:14]([C@H:10]4[C@H:11]([CH3:13])[CH2:12][NH:8][CH2:9]4)[NH:15][C:16](=[O:28])[C:17]=3[CH:22]=[N:21]2)[CH2:27][CH2:26][CH2:25][CH2:24]1.[ClH:29]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 135875901trans-6-(1-benzyl-4-methylpyrrolidin-3-yl)-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Product 2

HCID 313Hydrochloric AcidHCID 1361284551-cyclopentyl-6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-[(3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl]-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (9.25 g) in ethanol 100 mL was added to a Parr bottle. 2 mL of concentrated HCl followed by 3 g of palladium hydroxide was added. The reaction mixture was placed on a hydrogenator under 45 psi of H2 gas for 4 h. The reaction mixture was filtered through Celite and concentrated to provide the title compound as an HCl salt. 400 MHz 1H NMR (CDCl3) δ 8.00 (s, 1H), 5.14-5.10 (m, 1H), 4.89-3.84 (m, 1H), 3.72-3.67 (m, 1H), 3.38-3.31 (m, 1H), 3.03-2.98 (m, 1H), 2.85-2.81 (m, 1H), 2.08-1.85 (m, 7H), 1.69-1.61 (m, 2H), 1.19-1.10 (m, 3H). MS: (M+H m/z=288.2).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a2d14ac1ee104bf6a79dad04745bd70f
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

Loading…