Morpholine → N4-(6-aminopyridin-2-yl)-N6-phenylpyrimidine-4,6-diamine

HRID 2193633Notes

Reaction equation

HRID 2193633 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[N:10]=2)[CH:3]=1.[NH:16]1[CH2:21][CH2:20]OCC1.O.[Cl-].[Na+].O>C1COCC1>[NH2:15][C:11]1[N:10]=[C:9]([NH:8][C:4]2[CH:3]=[C:2]([NH:16][C:21]3[CH:20]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]=[CH:6][N:5]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 23713072Sodium chloride dihydrateHCID 57708264N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

Product 1

HCID 57708273N4-(6-aminopyridin-2-yl)-N6-phenylpyrimidine-4,6-diamineYield 127.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Fluoro-3-nitroaniline (1, 1 g, 1 equiv.) and morpholine (1.67 g, 3 equiv.) were dissolved in THF (10 mL). The reaction mixture was heated at reflux overnight. After cooling, water/brine (10 mL) was added, the mixture was agitated, and the layers were separated. The organic phase was dried over sodium sulfate, and the solvent was removed via rotary evaporation. The material was purified by flash chromatography using 0-40% gradient of heptane/EtOAc to give 800 mg of 3 as an orange-red solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. customthe layers were separated
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customthe solvent was removed via rotary evaporation
  7. customThe material was purified by flash chromatography

Sources & evidence

ORD record
ord-d3b8627221c6417aa94b6719e5cce933
Source dataset
uspto-grants-2012_12
Patent number
US08329901B2

Reaction notes

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