Cesium carbonate → 5-(6-Methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyrimidin-2-amine

HRID 2241809Notes

Reaction equation

HRID 2241809 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][O:9][C:5]=2[CH:4]=1.Br[C:13]1[CH:14]=[N:15][C:16]([N:19]([CH3:21])[CH3:20])=[N:17][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CC(P(C(C)(C)C)C(C)(C)C)(C)C.CC(P(C(C)(C)C)C(C)(C)C)(C)C.[Pd]>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[C:8]([C:13]3[CH:14]=[N:15][C:16]([N:19]([CH3:21])[CH3:20])=[N:17][CH:18]=3)[O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 127353155-Bromo-N,N-dimethylpyrimidin-2-amineHCID 190201846-Methoxybenzo[d]oxazole

Product 1

HCID 247806585-(6-Methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 6228DimethylformamideSolvent

Procedure

6-Methoxy-1,3-benzoxazole (0.67 mmol), 5-bromo-N,N-dimethylpyrimidin-2-amine (0.80 mmol), CuBr (0.13 mmol), Cs2CO3 (0.67 mmol) and Pd(t-Bu3P)2 (0.067 mmol) in dry DMF (3 ml) was stirred 30 min at 160° C. in a microwave reactor. The reaction mixture was filtered through celite, washed through with CH2Cl2 and the solvents were removed under reduced pressure. The crude product was purified by flash chromatography (CH2Cl2/CH2Cl2/MeOH (9:1) gradient) to give the title compound as an off white solid (108.2 mg). 1H NMR δ ppm 8.99 (s, 2H) 7.62 (d, 1H) 7.38 (d, 1H) 6.98 (dd, 1H) 3.83 (s, 3H) 3.23 (s, 6H); MS m/z 271 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed through with CH2Cl2
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was purified by flash chromatography (CH2Cl2/CH2Cl2/MeOH (9:1) gradient)

Sources & evidence

ORD record
ord-6ad30426728a4517a12a72f1324eace4
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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