Potassium Carbonate → HCID 14867563, compound

HRID 654595Notes

Reaction equation

HRID 654595 reaction equation
[CH:1]1([N:7]2[CH2:15][C:14]3[C:13](=[O:16])[N:12]4[N:17]=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:19]=[C:11]4[NH:10][C:9]=3[C:8]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:27](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH:1]1([N:7]2[CH2:15][C:14]3[C:13](=[O:16])[N:12]4[N:17]=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:19]=[C:11]4[N:10]([CH3:27])[C:9]=3[C:8]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 178515268HCID 178515268, compound

Product 1

HCID 14867563HCID 14867563, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 6-cyclohexyl-4,7-dihydro-2-phenyl-5H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8(6H)dione (2.00 g, 5.75 mmole) and potassium carbonate (795 mg, 5.75 mmole) in dry dimethylformamide (DMF, 30 mL) was added methyl idodide (0.72 mL, 12 mmole). The flask was stoppered tightly and stirred at room temperature for 24 hours. The mixture was diluted with water (150 mL), stirred for 10 minutes and suction filtered. The collected solid was washed once with water and once with 95% ethanol. Drying under vacuum left 1.91 g of white powdery solid. Crystallization from 95% ethanol (500 mL) afforded the titled product as fine white needles (1.73 g, 83%, m.p. 276°-279°). 1H NMR (CDCl3, δ) 8.05 (m, 2H, 2-phenyl H), 7.45 (m, 3H, 3,4-phenyl H), 6.45 (s, 1H, pyrazole-H), 4.33 (s, 2H, lactam CH2), 4.16 (s, 3H, CH3), 4.15 (m, 1H, cyclohexyl CH), 1.1-2.0 (m, 10H, cyclohexyl CH2); IR (mull, cm-1) 1693, 1627, 1590, 1574; UV (ethanol) λmax (ε) 206 (27,300), 226(23,920), 268(33,740), 285sh(15,570), 295(10,940), 338(6,090); MS m/e (rel. intens.) 363 (M+1, 25) 362 (M+, 100), 319(35), 280(66); Analysis calc'd for C21H22N4O2 =C, 65,59; H, 6.12 N, 15.46; Found=C, 69.64; H, 6.21; N, 15.43. TLC (silica, ethylacetate) Rf 0.80.

Workup

  1. additionwas added methyl idodide (0.72 mL, 12 mmole)
  2. stirringstirred for 10 minutes
  3. filtrationsuction filtered
  4. washThe collected solid was washed once with water and once with 95% ethanol
  5. customDrying under vacuum
  6. waitleft 1.91 g of white powdery solid
  7. customCrystallization from 95% ethanol (500 mL)

Sources & evidence

ORD record
ord-145ac72a1c734cb686d4f92632a09a20
Source dataset
uspto-grants-1992_07
Patent number
US05132424

Reaction notes

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