1,1'-Carbonyldiimidazole → HCID 178446079, compound

HRID 1787759Notes

Reaction equation

HRID 1787759 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[NH:8]/[C:7]/1=[N:16]/[NH2:17])[CH2:2][CH2:3][CH2:4][CH3:5].C1N=CN([C:23](N2C=NC=C2)=[O:24])C=1>C1COCC1>[OH:24][C:23]1[N:8]2[C:9](=[O:15])[C:10]3[NH:11][CH:12]=[N:13][C:14]=3[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]2=[N:16][N:17]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178446165HCID 178446165, compound

Product 1

HCID 178446079HCID 178446079, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (2z)-3-pentyl-3,7-dihydro-1h-purine-2,6-dione 2-hydrazone (200 mg, 0.846 mmol), N,N-carbonyldiimidazole (1.65 g, 10.2 mmol) in THF (10 ml) was stirred at 70° C. overnight. The reaction mixture was then heated in microwave reactor at 100° C. for 10 min. The reaction was completed checked by LCMS analysis. The reaction mixture was concentrated, diluted with EtOAc and washed with sat. NaHCO3. The aqueous was extracted with EtOAc (3×). The combined organic layers were dried (MgSO4) and concentrated to yield the desired product (230 mg, 98.4%). LCMS calculated for C11H15N6O2 (M+H) 263.1; found: 263.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with sat. NaHCO3
  4. extractionThe aqueous was extracted with EtOAc (3×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f989cf3c6a7f43c89ff1686e63ed6201
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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