Morpholine → 4-(2-Hydrazinyl-6-methyl-4-pyrimidinyl)morpholine

HRID 2074976Notes

Reaction equation

HRID 2074976 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.O.[NH2:17][NH2:18]>CO>[NH:17]([C:2]1[N:7]=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[C:4]([CH3:9])[N:3]=1)[NH2:18]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 24654Hydrazine hydrate (1:1)HCID 794712,4-Dichloro-6-methylpyrimidine

Product 1

HCID 668584764-(2-Hydrazinyl-6-methyl-4-pyrimidinyl)morpholineYield 59.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,4-dichloro-6-methylpyrimidine (0.41 g, 2.50 mmol) in MeOH (5 mL) was added morpholine (0.5 mL, 5.73 mmol). The solution was stirred for 30 min at room temperature, and then hydrazine monohydrate (1.0 mL, 20.6 mmol) was added. The solution was then heated at 60° C. and stirred for 16 h. The solution was then cooled to room temperature and purified by reverse phase HPLC to afford 0.31 g of the title compound (59%) as a waxy white solid. MH+210.

Workup

  1. temperatureThe solution was then heated at 60° C.
  2. stirringstirred for 16 h
  3. temperatureThe solution was then cooled to room temperature
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-da1608fe464742fc891b2316e834ad4b
Source dataset
uspto-grants-2011_04
Patent number
US07919528B2

Reaction notes

Loading…