4,6-Dimethoxy-2-(2-nitrobenzyl)pyrimidine → 2-(4,6-Dimethoxypyrimidin-2-ylmethyl)aniline

HRID 743976Notes

Reaction equation

HRID 743976 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)[N:4]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[N:4]=1

Participants

3

Reactant 1

HCID 539772304,6-Dimethoxy-2-(2-nitrobenzyl)pyrimidine

Product 1

HCID 537780302-(4,6-Dimethoxypyrimidin-2-ylmethyl)anilineYield 83.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of stage (i) (32.6 g) was added to a stirred suspension of stannous chloride dihydrate (133 g) in ethanol (300 ml). After refluxing for 2 hours, the solution was poured into ice-water (2500 ml) and extracted with ethyl acetate (3×500 ml). The combined extracts were washed with saturated sodium chloride solution, dried and evaporated to give 24.3 g of the desired product as a brown solid, mp 82°-84° C.

Workup

  1. temperatureAfter refluxing for 2 hours
  2. extractionextracted with ethyl acetate (3×500 ml)
  3. washThe combined extracts were washed with saturated sodium chloride solution
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-adf3e20eb4b147c39b65c2b8932dc558
Source dataset
uspto-grants-1996_09
Patent number
US05559081

Reaction notes

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