Hydrazine → 4-Hydrazinylpyrido[3,4-d]pyrimidine

HRID 1784377Notes

Reaction equation

HRID 1784377 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[CH:10][N:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:12][NH2:13]>C1COCC1>[N:5]1[C:4]2[CH:8]=[N:9][CH:10]=[CH:11][C:3]=2[C:2]([NH:12][NH2:13])=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 122716344-Chloropyrido(3,4-d)pyrimidine

Product 1

HCID 122716354-Hydrazinylpyrido[3,4-d]pyrimidineYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-Chloro-pyrido[3,4-d]pyrimidine (34)(1.65 g, 10 mmol) in anhydrous THF (10 ml) was added hydrazine (1M in THF, 30 ml, 30 mmol). The reaction mixture was stirred at room temperature for 5 hours whereupon a yellow precipitate formed. The solid was removed by filtration, washed with cold THF (10 ml) and dried to give the title compound (1.56 g, 96.9%) as the sole product which required no further purification. m/z (LC-MS, ESP): 162 [M+H]+, R/T=0.85 mins.

Workup

  1. customformed
  2. customThe solid was removed by filtration
  3. washwashed with cold THF (10 ml)
  4. customdried

Sources & evidence

ORD record
ord-287bfa590a71430eb724d3040f8e4c30
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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