Hydrazine → HCID 22046912, compound

HRID 2375180Notes

Reaction equation

HRID 2375180 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[N:5]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:3]=1.[NH2:21][NH2:22]>C1COCC1>[N:15]1([C:4]2[N:5]=[C:6]([O:8][C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)[N:7]=[C:2]([NH:21][NH2:22])[CH:3]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22046919HCID 22046919, compound

Product 1

HCID 22046912HCID 22046912, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-[6-chloro-2-(pyridin-3-yloxy)-pyrimidin-4-yl]-morpholine (295 mg, 1 mmol) in THF (10 mL) was added anhydrous hydrazine (0.320 ml, 10 mmol) under the nitrogen protection. The mixture was heated at 70° C. for 15 min. After cooling to room temperature, the reaction mixture was quenched by ice brine and extracted with EtOAc (100 mL). The organic phase was washed with brine (10 mL) and water (10 ml×2), dried (Na2SO4), filtered, evaporated, and purified by flash chromatography on a column of silica gel (CH2Cl2 and CH2Cl2-MeOH, 95:5) and to give [6-morpholin-4-yl-2-(pyridin-3-yloxy)-pyrimidin-4-yl-]-hydrazine (180 mg) in 62% yield. M/Z (M+1) 289.2

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was quenched by ice brine
  3. extractionextracted with EtOAc (100 mL)
  4. washThe organic phase was washed with brine (10 mL) and water (10 ml×2)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by flash chromatography on a column of silica gel (CH2Cl2 and CH2Cl2-MeOH, 95:5)

Sources & evidence

ORD record
ord-98e0a1e7b7c14e33897ffe5f5f1499ab
Source dataset
uspto-grants-2008_12
Patent number
US07465725B2

Reaction notes

Loading…