1,1'-Carbonyldiimidazole → 1-methyl-1H,4H,5H,6H,7H-pyrazolo(4,3-d)pyrimidine-5,7-dione

HRID 72180

Reaction equation

HRID 72180 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:10]([O-])=O)[CH:4]=[N:3]1.C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1>C(#N)C>[CH3:1][N:2]1[C:6]2[C:7](=[O:8])[NH:9][C:18](=[O:19])[NH:10][C:5]=2[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 18787291-methyl-4-nitro-1H-pyrazole-5-carboxamide

Product 1

HCID 99422421-methyl-1H,4H,5H,6H,7H-pyrazolo(4,3-d)pyrimidine-5,7-dioneYield 91.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

This compound was prepared following the method described in WO2008/071650. To a stirred solution of 1-methyl-4-nitro-1H-pyrazole-5-carboxamide (1.27 g, 9.06 mmol) in acetonitrile (35.6 mL) refluxed at 100° C. was added N,N-carbonyldimidazole (1.91 g, 11.78 mmol, 1.3 eq.) proportion wise over 1 hour. The reaction mixture was stirred at 100° C. under N2 for 18 hours. The resultant precipitate was filtered, rinsed well with cold acetonitrile, and pumped dry on high-vac to yield 1.38 g (91.5%) of a white solid. 1H NMR (DMSO-d6, 500 MHz) δ ppm 11.04 (broad d, 2H), 7.34 (s, 1H), 4.04 (s, 3H).

Workup

  1. customThis compound was prepared
  2. filtrationThe resultant precipitate was filtered
  3. washrinsed well with cold acetonitrile
  4. custompumped dry on high-vac

Sources & evidence

ORD record
ord-5f2cdd26af564967a8096d121173fb01
Source dataset
uspto-grants-2014_09
Patent number
US08828990B2

Linked notes

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