Morpholine → HCID 178422357, compound

HRID 1371125Notes

Reaction equation

HRID 1371125 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([CH3:12])=[N:11][C:3]=12.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>O>[CH3:8][C:6]1[NH:5][C:4]2[C:3]([N:11]=[C:10]([CH3:12])[CH:9]=2)=[C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:7]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 178422356HCID 178422356, compound

Product 1

HCID 178422357HCID 178422357, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 5-mL Wheaton vial was added 4-chloro-2,6-dimethylpyrrolo[3,2-d]pyrimidine (Example 46(d)) (0.10 g, 0.55 mmol) and morpholine (Aldrich Chemical Company) (0.24 mL, 2.7 mmol). A solution. of K2CO3 (0.35 g, 2.5 mmol) in water (2.5 mL) was added and the reaction mixture heated in the capped vial at reflux for 3.5 h. The reaction mixture was cooled to room temperature and the solution was filtered. The resulting precipitate was washed with H2O and hexanes and dried in a 60° C. vacuum oven to give 0.083 g (65%) of the title compound as an off-white solid. Mp: 242-243° C. 1H NMR (DMSO-d6; 500 MHz): δ 2.39 (s, 6), 3.60 (s, 4), 3.74 (s, 4), 6.07 (s, 1), 10.90 (s, 1). MS m/z: 233 (M+1). Anal. Calcd for C12H16N4O: C, 59.73; H, 7.10; N, 23.22. Found: C, 60.01; H, 6.84; N, 23.29.

Workup

  1. temperaturethe reaction mixture heated in the capped vial
  2. temperatureat reflux for 3.5 h
  3. filtrationthe solution was filtered
  4. washThe resulting precipitate was washed with H2O and hexanes
  5. customdried in a 60° C. vacuum oven

Sources & evidence

ORD record
ord-394e18ab4a544040982457a1cfdc013d
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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