Hydrochloric Acid → 6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1-tetrahydropyran-4-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424793Notes

Reaction equation

HRID 2424793 reaction equation
C([N:8]1[CH2:12][C@@H:11]([CH3:13])[C@H:10]([C:14]2[NH:15][C:16](=[O:29])[C:17]3[CH:22]=[N:21][N:20]([CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:18]=3[N:19]=2)[CH2:9]1)C1C=CC=CC=1.Cl>CO.[OH-].[Pd+2].[OH-]>[CH3:13][C@@H:11]1[CH2:12][NH:8][CH2:9][C@H:10]1[C:14]1[NH:15][C:16](=[O:29])[C:17]2[CH:22]=[N:21][N:20]([CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:18]=2[N:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 135886459PDE-9 inhibitor

Product 1

HCID 1361285606-[(3S,4S)-4-methylpyrrolidin-3-yl]-1-tetrahydropyran-4-yl-5H-pyrazolo[3,4-d]pyrimidin-4-oneYield 103.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

6-[(3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (5.6 g) was dissolved in 100 mL of methanol and added to a Parr bottle. Palladium hydroxide (3.76 g) was added along with 3.56 mL of concentrated hydrochloric acid. The reaction mixture was placed on a hydrogenator under 40 psi of H2 for 18 h. The reaction mixture was filtered through Celite and concentrated to provide 4.47 g of the title compound as the hydrogen chloride salt. 400 MHz 1H NMR (CD3OD) δ 8.03 (s, 1H), 4.49 (m, 1H), 4.09-4.06 (m, 2H), 3.74-3.57 (m, 4H), 3.24 (m, 1H), 3.05 (m, 1H), 2.89 (m, 1H), 2.77 (m, 1H), 2.30 (m, 2H), 1.90 (m, 2H), 1.22 (d, J=6.6 Hz, 3H). MS: (M+H m/z=304.2).

Workup

  1. additionadded to a Parr bottle
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-aa27a799581e4fdcbf1614784471872e
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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