Isoamyl Nitrite → 6-(6-Bromo-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-quinazoline

HRID 16029Notes

Reaction equation

HRID 16029 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:9][CH2:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][N:15]=[CH:14]3)[C:5]([NH2:8])=[N:6][CH:7]=1.[N:21](OCCC(C)C)=O>CN(C=O)C.CO>[Br:1][C:2]1[N:3]=[C:4]2[N:9]([CH2:10][C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][CH:20]=3)[N:17]=[CH:16][N:15]=[CH:14]4)[N:21]=[N:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 8053Isoamyl NitriteHCID 593419275-Bromo-N*3*-quinazolin-6-ylmethyl-pyrazine-2,3-diamine

Product 1

HCID 593418346-(6-Bromo-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-quinazolineYield 13%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To the solution of 5-bromo-N*3*-quinazolin-6-ylmethyl-pyrazine-2,3-diamine (1.02 g) in anhydrous DMF (12 mL) was added isoamyl nitrite (0.5 mL, 1.2 eq) at 0° C. dropwise. The ice bath was removed and the mixture was stirred for 5 minutes at room temperature, then at 70° C. for three hours. The reaction was cooled down to ambient temperature and quenched by 3 ml Sat'd Na2SO3. A precipitate was formed, and filtered. The mother liquor was extracted with ethyl acetate (2×200 ml) twice, and the combined extracts were washed twice by Sat'd NaHCO3 (2×100 ml), dried over Na2SO4, and concentrated to get the crude product which was dissolved in MeOH (10 ml), and a precipitate was formed. The solid was filtered to get 6-(6-Bromo-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-quinazoline (0.112 g, yield 13%).

Workup

  1. customThe ice bath was removed
  2. waitat 70° C. for three hours
  3. temperatureThe reaction was cooled down to ambient temperature
  4. customquenched by 3 ml Sat'd Na2SO3
  5. customA precipitate was formed
  6. filtrationfiltered
  7. extractionThe mother liquor was extracted with ethyl acetate (2×200 ml) twice
  8. washthe combined extracts were washed twice by Sat'd NaHCO3 (2×100 ml)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customto get the crude product which
  12. customa precipitate was formed
  13. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-d120469875764a24956e3896adf6adb6
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Reaction notes

Loading…