4-(Tri-n-butylstannyl)pyridine → 4-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyridin-4-yl-pyrimidine

HRID 965689노트

반응식

HRID 965689 반응식
Cl[C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[N:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:23][C:22]1[C:17]([C:13]2[N:12]([CH2:11][C:6]3[C:7]([CH2:8][CH2:9][CH3:10])=[C:2]([C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)[N:3]=[CH:4][N:5]=3)[CH:16]=[CH:15][N:14]=2)=[N:18][CH:19]=[CH:20][CH:21]=1

참가 물질

5

반응물 2

HCID 27373184-(Tri-n-butylstannyl)pyridineHCID 100423524-Chloro-6-{[2-(3-fluoro-2-pyridinyl)-1H-imidazol-1-yl]methyl}-5-propylpyrimidine

생성물 1

HCID 100908044-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyridin-4-yl-pyrimidine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine (268 mg, 0.81 mmol), 4-tributylstannanyl-pyridine (1.21 mmol), Pd(PPh3)4 (0.08 mmol, 93 mg) in toluene (10 mL) is degassed. The mixture is then heated at 100° C. overnight. Saturated KF aqueous solution (8 mL) is added and the mixture is stirred for 15 minutes. The layers are separated and the aqueous layer is extracted with EtOAc (10 mL). The combined extracts are washed with brine (15 mL), dried (Na2SO4), and evaporated. Preparative TLC (5% methanol in DCM) purification of the residue provides the title product. 1H NMR (CDCl3) 8.95 (s, 1H), 8.65 (d, 1H), 8.26 (d, 1H), 7.77-7.84 (m, 2H), 7.49 (t, 1H), 7.34 (t, 1H), 7.30 (s, 1H), 7.19-7.22 (m, 1H), 7.14 (s, 1H), 5.92 (s, 2H), 2.87-2.91 (m, 2H), 1.46-1.52 (m, 2H), 0.81 (t, 3H).

후처리

  1. customis degassed
  2. additionSaturated KF aqueous solution (8 mL) is added
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 mL)
  5. washThe combined extracts are washed with brine (15 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPreparative TLC (5% methanol in DCM) purification of the residue

출처 및 근거

ORD 기록
ord-d343c5a7b91f4942af61dd211ec110b6
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951864B2

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