Diazomethane → HCID 13565430, compound

HRID 1194660Notes

Reaction equation

HRID 1194660 reaction equation
[CH2:1]([N:8]1[C:13]2=[N:14][C:15]3[N:16]([CH3:24])[C:17](=[O:23])[N:18]([CH3:22])[C:19](=[O:21])[C:20]=3[N:12]2[C:11]([OH:25])=[C:10]([CH2:26][CH2:27][CH3:28])[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:32])=[N-]>C(Cl)(Cl)Cl>[CH3:24][N:16]1[C:15]2[N:14]=[C:13]3[N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:9](=[O:29])[C:10]([CH2:26][CH2:27][CH3:28])=[C:11]([O:25][CH3:32])[N:12]3[C:20]=2[C:19](=[O:21])[N:18]([CH3:22])[C:17]1=[O:23]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 178439743HCID 178439743, compound

Product 1

HCID 13565430HCID 13565430, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolve 9-benzyl-1,3-dimethyl-6-hydroxy-7-(n-propyl)-pyrimido[2,1-f]purine-2,4,8(1H,3H,9H)-trione (3 g) in 200 ml chloroform at 0° C. and treate with an ethereal solution of diazomethane. Stir the solution at 0° for 1.5 hours and destroy the excess diazomethane by the addition of acetic acid. Wash the chloroform solution with a solution of sodium bicarbonate and remove the chloroform under reduced pressure. Chromatograph the solid obtained on silica gel using 1% methanol in chloroform to give the title compound, mp 199°-201° C.

Workup

  1. customdestroy the excess diazomethane
  2. additionby the addition of acetic acid
  3. washWash the chloroform solution with a solution of sodium bicarbonate
  4. customremove the chloroform under reduced pressure
  5. customobtained on silica gel using 1% methanol in chloroform

Sources & evidence

ORD record
ord-5b5e1d723dfd46f6bbc086b2d3939f0e
Source dataset
uspto-grants-1989_03
Patent number
US04816458

Reaction notes

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