Hydrogen Peroxide → 2-(4-Phenyl-butyl)-3H-pyrimido[4,5-d]pyrimidin-4-one

HRID 2076811Notes

Reaction equation

HRID 2076811 reaction equation
C([O-])([O-])=[O:2].[K+].[K+].[C:7]([C:9]1[C:10]([NH:15][C:16](=O)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:11][CH:12]=[N:13][CH:14]=1)#[N:8].OO>CO.CS(C)=O.C(OCC)(=O)C>[C:21]1([CH2:20][CH2:19][CH2:18][CH2:17][C:16]2[NH:8][C:7](=[O:2])[C:9]3[C:10]([N:15]=2)=[N:11][CH:12]=[N:13][CH:14]=3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 670991235-Phenyl-pentanoic acid (5-cyano-pyrimidin-4-yl)-amide

Product 1

HCID 1359235202-(4-Phenyl-butyl)-3H-pyrimido[4,5-d]pyrimidin-4-oneYield 1.8%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an atmosphere of nitrogen, K2CO3 (3.057 g) was added to a solution of 5-phenyl-pentanoic acid (5-cyano-pyrimidin-4-yl)-amide (1.00 g) in MeOH (5 ml) and DMSO (1.2 ml). The mixture was cooled (ice bath) and hydrogen peroxide (35% in H2O, 1.5 ml) was added dropwise. The mixture was taken up in ethyl acetate and washed with water. The organic layer was dried (Na2SO4), filtered, and the solvent was evaporated. 2-(4-Phenyl-butyl)-3H-pyrimido[4,5-d]pyrimidin-4-one (18 mg, 1.8%) was obtained from the residue by subsequent column chromatography (silica gel, eluent gradient n-heptan/ethyl acetate=100:0-60:40) and preparative, reverse-phase HPLC (Agilent Zorbax XdB C18 column, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 7 min, flow rate 30 ml/min). MS: m/e=279.3 [M−H−]. 1H NMR (d6-DMSO): δ 1.62-2.00 (m, 4H), 2.55-2.80 (m, 4H), 7.17-7.18 (m, 2H), 7.26-7.28 (m, 3H), 9.56 (d, 1H), 9.64 (d, 1H), 11.13 (bs, 1H).

Workup

  1. additionwas added dropwise
  2. washwashed with water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-39e3204b7dec40dfa23c7aff44015941
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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