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

HRID 2241809ノート

反応式

HRID 2241809 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)触媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6ad30426728a4517a12a72f1324eace4
出典データセット
uspto-grants-2010_03
特許番号
US07670591B2

反応ノート

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