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

HRID 2241809노트

반응식

HRID 2241809 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6ad30426728a4517a12a72f1324eace4
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07670591B2

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