Water → HCID 178489842, compound

HRID 2367386Notes

Reaction equation

HRID 2367386 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH:14]3[O:19][CH2:18][CH2:17][NH:16][CH2:15]3)[NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:20][C:21]1[CH:26]=[C:25](Cl)[N:24]=[C:23]([NH2:28])[N:22]=1.CCN(C(C)C)C(C)C.O>C(O)C>[Cl:20][C:21]1[CH:26]=[C:25]([N:16]2[CH2:17][CH2:18][O:19][CH:14]([C:11]3[NH:12][CH:13]=[C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:10]=3)[CH2:15]2)[N:24]=[C:23]([NH2:28])[N:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 178489844HCID 178489844, compound

Product 1

HCID 178489842HCID 178489842, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-{4-[3-(methyloxy)phenyl]-1H-imidazol-2-yl}morpholine (1.5 g, 5.07 mmol) and 4,6-dichloro-2-pyrimidinamine (0.832 g, 5.07 mmol) in ethanol (100 mL) was added Hunig's base (4.5 mL, 25.4 mmol), and the reaction mixture was stirred overnight at reflux. Water (150 mL) was added, and the resulting mixture was extracted with EtOAc (3×100 mL). The organic was dried (Na2SO4), filtered, and concentrated. Purification by silica gel chromatography, eluting with EtOAc in PE from 50% to 80% afforded the title compound (830 mg) as a brown solid. LC-MS (ES) m/z=387 [M+H]+.

Workup

  1. temperatureat reflux
  2. extractionthe resulting mixture was extracted with EtOAc (3×100 mL)
  3. dry with materialThe organic was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography
  7. washeluting with EtOAc in PE from 50% to 80%

Sources & evidence

ORD record
ord-8ba26386ab944ac99da70b942c6a4be1
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…