2-Aminopyridine → 2,4-Disubstituted Pyrimidine 4a

HRID 968249노트

반응식

HRID 968249 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].CS([C:14]1[N:19]=[C:18]([N:20]2[CH:24]=[CH:23][N:22]=[C:21]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:17]=[CH:16][N:15]=1)(=O)=O>C1COCC1>[C:25]1([C:21]2[N:20]([C:18]3[CH:17]=[CH:16][N:15]=[C:14]([NH:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=4)[N:19]=3)[CH:24]=[CH:23][N:22]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

참가 물질

5

반응물 3

HCID 104392-AminopyridineHCID 24758Sodium hydrideHCID 22288411HCID 22288411, 화합물

생성물 1

HCID 53294302,4-Disubstituted Pyrimidine 4a

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-aminopyridine (31 mg, 0.33 mmol) in dry THF (0.5 mL) was added NaH (32 mg, 1.33 mmol) at room temperature. Once the resulting bubbling had ceased, 2-(methylsulfonyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine (0.100 g, 0.33 mmol) was added all at once. After 1.5 hours the mixture was concentrated in vacuo, diluted with water and the pH of the resulting solution was adjusted to 7 with 1M HCl (aq). The resulting precipitate was filtered and purified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA). 1H-NMR (300 MHz, CDCl3) δ 8.44 (d overlapping with s, J=5.4 Hz, 2H), 8.33 (d, J=4.1 Hz, 1H), 7.93 (d, J=8.3 Hz, 1H), 7.55 (m, 4H), 7.40 (m, 3H), 7.33 (m, 1H), 6.95 (dd, J=4.9, 7.1 Hz, 1H), 6.45 (d, J=5.3 Hz, 1H).

후처리

  1. customOnce the resulting bubbling
  2. concentrationAfter 1.5 hours the mixture was concentrated in vacuo
  3. additiondiluted with water
  4. filtrationThe resulting precipitate was filtered
  5. custompurified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA)

출처 및 근거

ORD 기록
ord-2b6dfdd04cfb4d87a3148b9da5e0c9ba
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958340B2

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