2,4-Dibenzyloxy-6-(2-dimethylaminovinyl)-5-nitropyrimidine → HCID 178420407, compound

HRID 1976545Notes

Reaction equation

HRID 1976545 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([N+:23]([O-])=O)=[C:11]([CH:26]=[CH:27]N(C)C)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[CH2:1]([O:8][C:9]1[NH:10][C:11]2=[CH:26][CH:27]=[N:23][C:12]2=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 541062272,4-Dibenzyloxy-6-(2-dimethylaminovinyl)-5-nitropyrimidine

Product 1

HCID 178420407HCID 178420407, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (30 g) was added to a solution of the product from Example 36.2 (20 g) in acetic acid (300 ml) with cooling to control the exotherm. The resulting mixture was then stirred for 2 h, filtered, and the filtrate was concentrated to dryness. The residue was partioned between chloroform and aqueous sodium bicarbonate, the organic layer was dried and then concentrated to dryness to give a solid residue of 2,4-dibenzyloxypyrrolo[3,2-d]pyrimidine (15.2 g).

Workup

  1. temperaturewith cooling
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated to dryness
  4. customthe organic layer was dried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-da39e5393639471c824dbe80d3a13803
Source dataset
uspto-grants-2001_05
Patent number
US06228847B1

Reaction notes

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