2,4,6-Trichloropyrimidine → HCID 72942068, compound

HRID 538922Notes

Reaction equation

HRID 538922 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.CCN(C(C)C)C(C)C.[CH3:19][C@H:20]1[CH2:25][O:24][CH2:23][CH2:22][NH:21]1>O1CCOCC1.CCOC(C)=O>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][C@@H:20]2[CH3:19])[N:3]=1

Participants

6

Reactant 3

HCID 773782,4,6-TrichloropyrimidineHCID 81531DiisopropylethylamineHCID 12012220(3S)-3-methylmorpholine

Product 1

HCID 72942068HCID 72942068, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

The 2,4,6-trichloropyrimidine (100 mg, 053 mmol) was dissolved in dioxane (2 mL) with DIPEA (280 μL, 1.6 mmol) and (S)-3-methylmorpholine (54 mg, 0.53 mmol). The reaction mixture was heated at 130° C. under microwave irradiations for 15 min. It was then diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by preparative HPLC (Waters Sun Fire C18, 30×100 mm, 5 um; 0.1% TFA-water/acetonitrile; gradient acetonitrile 5-100% in 20 min) to afford the title compound (45 mg, 34%). tR: 3.70 min (HPLC 1); ESI-MS: 248.2/250.2 [M+H]+ (LC-MS 1).

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC (Waters Sun Fire C18, 30×100 mm, 5 um; 0.1% TFA-water/acetonitrile; gradient acetonitrile 5-100% in 20 min)

Sources & evidence

ORD record
ord-441a7cc7624c428aa34ea64df72cbb1d
Source dataset
uspto-grants-2014_10
Patent number
US08865894B2

Reaction notes

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