Dichloromethane → HCID 53812533, compound

HRID 1068570Notes

Reaction equation

HRID 1068570 reaction equation
[N:1]1([C:10]2[N:15]=[C:14](Cl)[CH:13]=[C:12]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH-].[Na+].[CH3:25][C@H:26]1[O:31][C@@H:30]([CH3:32])[CH2:29][NH:28][CH2:27]1.C(Cl)Cl>O1CCOCC1.O.O>[N:1]1([C:10]2[N:15]=[C:14]([N:28]3[CH2:27][C@@H:26]([CH3:25])[O:31][C@@H:30]([CH3:32])[CH2:29]3)[CH:13]=[C:12]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 6415002,6-Dimethylmorpholine, cis-HCID 10734147HCID 10734147, compound

Product 1

HCID 53812533HCID 53812533, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To the obtained 2-(benzimidazol-1-yl)-4-chloro-6-morpholinopyrimidine (318 mg, 1.00 mmol) dissolved in dioxane—water solution (4:1), sodium hydroxide (100 mg, 4.3 mmol) and cis-2,6-dimethylmorpholine (126 mg, 1.20 mmol) were added and stirred at 80° C. for 12 hours. The reaction mixture was condensed under reduced pressure and the obtained residue was mixed with methylene chloride and water and shaken. Organic layer was separated from the mixture and washed with water and dried over anhydrous magnesium sulfate. The solvent was removed out under reduced pressure and the residue was purified by silica gel column chromatography to obtain 340 mg of the titled compound (yield: 86%).

Workup

  1. customcondensed under reduced pressure
  2. stirringshaken
  3. customOrganic layer was separated from the mixture
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed out under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ae29f5816aa743b9a0caa6b03b4031a2
Source dataset
uspto-grants-2001_06
Patent number
US06251900B1

Reaction notes

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