Water → HCID 178437889, compound

HRID 1600805Notes

Reaction equation

HRID 1600805 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([CH2:16][OH:17])=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:18][CH3:19])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].O>C(Cl)Cl>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([CH2:16][O:17][S:28]([CH3:27])(=[O:30])=[O:29])=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:18][CH3:19])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178437888HCID 178437888, compound

Product 1

HCID 178437889HCID 178437889, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of 1-cyclopentyl-3-ethyl-6-(hydroxymethyl) pyrazolo[3,4-d]pyrimidin-4-one (1.0 g, 3.8 mmol), CH2Cl2 (25 mL) and triethylamine (0.77 g, 7.6 mmol) at -50° C. was added methanesulfonyl chloride (0.44 g, 3.8 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred for 1 hour, CH2Cl2 and water were added and the organic layer was separated, dried over MgSO4, filtered and concentrated in vacuo to afford 1.28 g of crude product. The crude product was combined with that from a similar experimental run and the mixture was recrystallized from ether (2×) to afford 1-cyclopentyl-3-ethyl-6-(methylsulfonyloxymethyl) pyrazolo[3,4-d]pyrimidin-4-one, m.p. 138-140° C.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford 1.28 g of crude product
  6. customthe mixture was recrystallized from ether (2×)

Sources & evidence

ORD record
ord-567db2e807f34fedae9d8f051e3636b7
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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