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

HRID 965689Notes

Reaction equation

HRID 965689 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d343c5a7b91f4942af61dd211ec110b6
Source dataset
uspto-grants-2005_10
Patent number
US06951864B2

Reaction notes

Loading…