Ethanol → HCID 14867562, compound

HRID 654594Notes

Reaction equation

HRID 654594 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(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O)C>CN(C=O)C.O.C(Cl)(Cl)Cl.C(OC(=O)C)C>[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]([CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:9]=3[C:8]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 702EthanolHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178515268HCID 178515268, compound

Product 1

HCID 14867562HCID 14867562, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21584013Chloroform ethylacetateSolvent

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, prepared as described in Preparation 1 hereinabove, (2.00 g., 5.74 mmoles) and anhydrous potassium carbonate (795 mg., 5.75 mmole) in dry DMF (30 ml. in a flask there was added benzyl bromide (1.37 ml., 11.5 mmoles). The flask was stoppered tightly and stirred at room temperature for 24 hours. The mixture was diluted with water (150 ml.), stirred for 30 minutes and suction filtered. The collected solid was washed twice more water and air dried. The resulting solid was crystallized from an ethanol/chloroform, about 3/1 V/V ratio, 650 ml., dissolved at reflux temperature of the mixture and then cooled to 0° C. to afford 2.11 g. of the tilted product as fine, ivory colored needle crystals (84% yield,, m.p. 276°-278° C.). 1H NMR (CDCl3) 8.0 (m,2H, pyrazole o-phenyl), 7.3-7.5 (m,8H, phenyl), 6.44 (s, 1H, pyrazole-H), 5.93 (s, 2H, CH2 phenyl), 4.41 (s, 2H, lactam CH2), 4.18 (m, 1H, cyclohexyl CH), 1.1-2.0 (m, 10H, cyclohexyl CH2); IR (mull, cm1) 1697, 1679, 1618, 1591, 1577; UV (ethanol) λ max (ε)205(35,680), 227(23,860), 267(33,080), 285 sh (15,450), 295 sh (11,460) 338 (6,870); MS m/e (rel. intens.) 438(M+,15), 347(5), 91(100); Anal. calcd. for C27H26N4O2 : % Calcd.: C, 73.95; H, 5.98; N, 12.78; % Found: C, 73.88; H, 6.07; N, 12.80. TLC (silica, 4/1 V/V chloroform/ethylacetate) Rf 0.56.

Workup

  1. customprepared
  2. stirringstirred for 30 minutes
  3. filtrationsuction filtered
  4. washThe collected solid was washed twice more water and air
  5. customdried
  6. customThe resulting solid was crystallized from an ethanol/chloroform, about 3/1 V/V ratio, 650 ml
  7. dissolution, dissolved
  8. temperatureat reflux temperature of the mixture
  9. temperaturecooled to 0° C.
  10. customto afford 2.11 g

Sources & evidence

ORD record
ord-85b7b465d8f54013bf6319d2ce763fd3
Source dataset
uspto-grants-1992_07
Patent number
US05132424

Reaction notes

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