1,1'-Carbonyldiimidazole → HCID 178446079, compound

HRID 2368562Notes

Reaction equation

HRID 2368562 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-dde1a531f36c4f32ae34425079e23a35
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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