m-Tolyl isocyanate → HCID 178425508, compound

HRID 2218204Notes

Reaction equation

HRID 2218204 reaction equation
[NH2:1][C:2]1[C:3]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[N:4][C:5]([O:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:6][C:7]=1[NH2:8].[C:25]1([CH3:34])[CH:30]=[CH:29][CH:28]=[C:27]([N:31]=[C:32]=O)[CH:26]=1>C1COCC1>[N:19]1([C:3]2[N:4]=[C:5]([O:9][CH2:10][CH2:11][O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:6]=[C:7]3[C:2]=2[N:1]=[C:32]([NH:31][C:27]2[CH:26]=[C:25]([CH3:34])[CH:30]=[CH:29][CH:28]=2)[NH:8]3)[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 587181926-(Morpholin-4-yl)-2-{2-[(pyridin-2-yl)oxy]ethoxy}pyrimidine-4,5-diamine

Product 1

HCID 178425508HCID 178425508, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5,6-Diamino-2-[2-(pyridin-2-yloxy)-ethoxy]4-morphlinopyrimidine (0.332 g, 1.00 mmol, 1.00 equiv.) and m-tolyl isocyanate (0.133 g, 1.00 mmol, 1.00 equiv.) were mixed in 10 mL THF and stirred at room temperature for 15 hours. THF was removed, and the residue was treated with POCl3 in 2 mL CH3NO2 at 100° C. for 30 minutes. The reaction mixture was neutralized with 2N NaOH solution at 0° C., and subjected to EtOAc extraction. The organic solution was dried over MgSO4, filtered through a plug of silica gel, concentrated to around 2 mL, and cooled to 0° C., resulting in formation of the titled compound as off-white crystal which was collected by filtration, washed with EtOAc, and dried (0.095 g, 0.212 mmol, 21.2% yield).

Workup

  1. customTHF was removed
  2. additionthe residue was treated with POCl3 in 2 mL CH3NO2 at 100° C. for 30 minutes
  3. customwas neutralized with 2N NaOH solution at 0° C.
  4. extractionsubjected to EtOAc extraction
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered through a plug of silica gel
  7. concentrationconcentrated to around 2 mL
  8. temperaturecooled to 0° C.

Sources & evidence

ORD record
ord-bf2549d9fc554ae9a2ac6a22ccce0638
Source dataset
uspto-grants-2008_08
Patent number
US07410990B2

Reaction notes

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