Water → HCID 178437882, compound

HRID 2257047Notes

Reaction equation

HRID 2257047 reaction equation
Cl.[CH2:2]([N:4]([CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)[CH2:5][CH3:6])[CH3:3].O1CCOCC1.[CH:23]1([N:28]2[C:32]3=[N:33][C:34]([CH2:38][C:39]4[CH:44]=[CH:43][C:42](O)=[CH:41][CH:40]=4)=[N:35][C:36](=[O:37])[C:31]3=[C:30]([CH2:46][CH3:47])[NH:29]2)[CH2:27][CH2:26][CH2:25][CH2:24]1.O>C(OCC)(=O)C>[CH:23]1([N:28]2[C:32]3=[N:33][C:34]([CH2:38][C:39]4[CH:40]=[CH:41][C:42]([O:13][C:12]([C:11]5[CH:10]=[CH:9][C:8]([CH2:7][N:4]([CH2:5][CH3:6])[CH2:2][CH3:3])=[CH:16][CH:15]=5)=[O:14])=[CH:43][CH:44]=4)=[N:35][C:36](=[O:37])[C:31]3=[C:30]([CH2:46][CH3:47])[NH:29]2)[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 312751,4-Dioxane2×HCID 122990074-((Diethylamino)methyl)benzoic acid hydrochlorideHCID 178437877HCID 178437877, compound

Product 1

HCID 178437882HCID 178437882, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-diethylaminomethyl benzoic acid hydrochloride (360 mg, 1.5 mmol), N,N'-carbonyldiimidazole (264 mg, 1.5 mmol) and dioxane (20 ml) was heated on an oil bath for 1 hour. The reaction mixture was cooled to room temperature and 1-cyclopentyl-3-ethyl-6-(4-hydroxyphenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one (500 mg, 105 mmol) and dioxane (10 ml) were added and the reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled, the solvent was stripped and then water and ethyl acetate were added. The ethyl acetate layer was separated, then washed with 2N HCl (4×150 ml). The aqueous layers were combined, treated with concentrated NH4OH and then extracted with ethyl acetate (2×). The ethyl acetate layer was washed with brine, dried over MgSO4, filtered and stripped to afford crude product. The crude product was combined with the crude product from a similar experimental run and the mixture was recrystallized from ether to afford 0.46 g of 1-cyclopentyl-3-ethyl-6-[4-[4-(diethylaminomethyl)phenylcarbonyloxy]phenylmethyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 143°-145° C.

Workup

  1. temperaturewas heated on an oil bath for 1 hour
  2. temperaturethe reaction mixture was heated at 100° C. overnight
  3. temperatureThe reaction mixture was cooled
  4. customThe ethyl acetate layer was separated
  5. washwashed with 2N HCl (4×150 ml)
  6. additiontreated with concentrated NH4OH
  7. extractionextracted with ethyl acetate (2×)
  8. washThe ethyl acetate layer was washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customto afford crude product
  12. customthe mixture was recrystallized from ether

Sources & evidence

ORD record
ord-be35d3c4b26f45ec8707790a0d712094
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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