Potassium Carbonate → 4-Chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-methyl-5-propyl-pyrimidine

HRID 965686노트

반응식

HRID 965686 반응식
[CH2:1]([C:4]1[C:5]([Cl:12])=[N:6][CH:7]=[N:8][C:9]=1[CH2:10]Br)[CH2:2][CH3:3].[F:13][C:14]1[C:15]([C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)=[N:16][CH:17]=[CH:18][CH:19]=1.[C:25]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:12][C:5]1[C:4]([CH2:1][CH2:2][CH3:3])=[C:9]([CH2:10][N:24]2[CH:23]=[CH:22][N:21]=[C:20]2[C:15]2[C:14]([F:13])=[CH:19][CH:18]=[CH:17][N:16]=2)[N:8]=[C:7]([CH3:25])[N:6]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 223131604-Bromomethyl-5-propyl-6-chloro-pyrimidineHCID 223131643-Fluoro-2-(1H-imidazol-2-yl)pyridine

생성물 1

HCID 99977004-Chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-methyl-5-propyl-pyrimidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 5-propyl-6-bromomethyl-4-chloro-pyrimidine (1 mmol), 3-fluoro-2-(1H-imidazol-2-yl)-pyridine (163 mg, 1 mmol), and K2CO3 (552 mg, 4 mmol) in DMF (6 mL) is stirred at room temperature overnight. The solvent is removed in vacuo and EtOAc (10 mL) and water (10 mL) are added to the residue. The layers are separated and the aqueous layer is extracted with EtOAc (10 mL). The combined extracts are washed with brine (10 mL), dried (Na2SO4), and evaporated. Preparative TLC separation of the residue with 5% MeOH in CH2Cl2 provides the title compound as a white solid. 1H-NMR (CDCl3) δ: 8.65 (S, 1H), 8.24 (d, 1H), 7.53 (t, 1H), 7.32 (s, 1H), 7.27-7.22 (m, 1H), 7.12 (s, 1H), 5.87 (s, 2H), 2.76 (t, 2H), 1.68-1.54 (m, 2H), 1.01 (t, 3H).

후처리

  1. customThe solvent is removed in vacuo and EtOAc (10 mL) and water (10 mL)
  2. additionare added to the residue
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 mL)
  5. washThe combined extracts are washed with brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPreparative TLC separation of the residue with 5% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-5a42393d343846b98da02358bcffce09
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951864B2

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