Methanol → 4-(3-(4-(4,6-Dimorpholino-1,3,5-triazin-2-yl)phenyl)ureido)benzoic acid

HRID 1513428Notes

Reaction equation

HRID 1513428 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:38])[NH:27][C:28]4[CH:37]=[CH:36][C:31]([C:32]([O:34]C)=[O:33])=[CH:30][CH:29]=4)=[CH:21][CH:20]=3)[N:8]=2)[CH2:3][CH2:2]1.C1COCC1.CO.O[Li].O>O>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[N:12]=[C:11]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[N:10]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:38])[NH:27][C:28]4[CH:37]=[CH:36][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=4)=[CH:21][CH:20]=3)[N:8]=2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 44515696Methyl 4-[({4-[bis(morpholin-4-yl)-1,3,5-triazin-2-yl]phenyl}carbamoyl)amino]benzoate

Product 1

HCID 445163074-(3-(4-(4,6-Dimorpholino-1,3,5-triazin-2-yl)phenyl)ureido)benzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of methyl 4-(3-(4-(4,6-dimorpholino-1,3,5-triazin-2-yl)phenyl)ureido)benzoate (1.4 g, 2.69 mmol), THF (10 mL), MeOH (5 mL) and H2O (2.5 mL) was added LiOH.H2O (339 mg, 8.07 mmol) then heated under reflux for 8 hrs. Concentrated and added H2O (5 mL) then acidified with 2N HCl. The solid was filtered washed with H2O and dried to give the product as a tan solid (1.3 g, 96% yield); MS (ESI) m/z=506.3

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 8 hrs
  3. concentrationConcentrated
  4. additionadded H2O (5 mL)
  5. filtrationThe solid was filtered
  6. washwashed with H2O
  7. customdried

Sources & evidence

ORD record
ord-0292008bf59341f3bd7a3d4652872497
Source dataset
uspto-grants-2012_07
Patent number
US08217036B2

Reaction notes

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