[(2-Chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]-acetic acid ethyl ester → 2-chloro-8-isopropyl-7,8-dihydro-5H-pteridin-6-one

HRID 1957986Notes

Reaction equation

HRID 1957986 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([C:10]1[C:15]([N+:16]([O-])=O)=[CH:14][N:13]=[C:12]([Cl:19])[N:11]=1)[CH:7]([CH3:9])[CH3:8])C.[H][H]>C1COCC1.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.O=[V]>[Cl:19][C:12]1[N:13]=[CH:14][C:15]2[NH:16][C:4](=[O:3])[CH2:5][N:6]([CH:7]([CH3:9])[CH3:8])[C:10]=2[N:11]=1

Participants

5

Reactant 2

HCID 59286164[(2-Chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]-acetic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 592861702-chloro-8-isopropyl-7,8-dihydro-5H-pteridin-6-oneYield 87%

Reagents, catalysts & solvents 2

HCID 5377696Vanadium, oxobis(2,4-pentanedionato-O,O')-, (SP-5-21)-CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of [(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]-acetic acid ethyl ester (40 g; 0.132 mol), Pt/C5% (2 g) and vanadylacetylacetonate (2 g; 0.754 mmol) in THF (50 ml) was treated with hydrogen (5 bar) overnight. The reaction mixture was warmed (in order to solubilize the precipitate formed) and filtered on a celite pad, then concentrated in vacuo. The crude was diluted in ethyl acetate and the organic phase was washed with NaOH 10% solution, dried with MgSO4 and concentrated in vacuo. 28 g (0.115 mol; 87% yield) of solid material were obtained.

Workup

  1. temperatureThe reaction mixture was warmed (in order
  2. customformed) and
  3. filtrationfiltered on a celite pad
  4. concentrationconcentrated in vacuo
  5. additionThe crude was diluted in ethyl acetate
  6. washthe organic phase was washed with NaOH 10% solution
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated in vacuo
  9. custom28 g (0.115 mol; 87% yield) of solid material were obtained

Sources & evidence

ORD record
ord-18b71f5916af4ecd8471bdb1ccd457dc
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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