Triethylamine → N-(6-Methoxy-2-pyrazinyl)-Na(2)-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea

HRID 2273088Notes

Reaction equation

HRID 2273088 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[O:3]1.C(N(CC)CC)C.ClC(Cl)(O[C:28](=O)[O:29][C:30](Cl)(Cl)Cl)Cl.C[O:37][C:38]1[N:43]=[C:42]([NH2:44])[CH:41]=[N:40][CH:39]=1>C(Cl)Cl.O>[CH3:30][O:29][C:28]1[N:44]=[C:42]([NH:43][C:38]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)=[O:37])[CH:41]=[N:40][CH:39]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 48681936-Methoxypyrazin-2-amine

Product 1

HCID 89714525N-(6-Methoxy-2-pyrazinyl)-Na(2)-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaYield 28.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 350 mg (1.60 mmol) of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenylamine and 1.35 ml (9.59 mmol) of triethylamine in 10 ml of DCM is added, under nitrogen, to a solution of 474.07 mg (1.60 mmol) of triphosgene in 30 ml of DCM. The mixture is stirred for 30 minutes at room temperature, followed by addition of 1 g (7.99 mmol) of 6-methoxypyrazin-2-amine. The resulting mixture is stirred for 2 hours at room temperature. Water is added and the product is extracted with DCM. The solution is dried over MgSO4 and then filtered. The filtrate is evaporated under reduced pressure and the residue is then chromatographed on silica gel, eluting with a DCM/MeOH mixture from (100/0 v/v) up to (96/4 v/v). The solvent is evaporated off under reduced pressure. The residue is taken up in ethyl acetate and washed three times with 1N hydrochloric acid solution and then with saturated NaCl solution. The resulting solution is dried over MgSO4. 167 mg of 1-(6-methoxypyrazin-2-yl)-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]urea are obtained.

Workup

  1. stirringThe resulting mixture is stirred for 2 hours at room temperature
  2. extractionthe product is extracted with DCM
  3. dry with materialThe solution is dried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate is evaporated under reduced pressure
  6. customthe residue is then chromatographed on silica gel
  7. washeluting with a DCM/MeOH mixture from (100/0 v/v) up to (96/4 v/v)
  8. customThe solvent is evaporated off under reduced pressure
  9. washwashed three times with 1N hydrochloric acid solution
  10. dry with materialThe resulting solution is dried over MgSO4

Sources & evidence

ORD record
ord-1b53a6a027bc4a43b9f6cad3a5c3a095
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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