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Cesium carbonate → 4-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyridin-3-yl-pyrimidine

HRID 965690
Notes
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Reaction equation

HRID 965690 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.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[CH:25]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[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:26]4[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=4)[N:3]=[CH:4][N:5]=3)[CH:16]=[CH:15][N:14]=2)=[N:18][CH:19]=[CH:20][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27343783-Pyridinylboronic acidHCID 100423524-Chloro-6-{[2-(3-fluoro-2-pyridinyl)-1H-imidazol-1-yl]methyl}-5-propylpyrimidine

Product 1

HCID 100680004-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyridin-3-yl-pyrimidine

Reagents, catalysts & solvents

2
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

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), 3-pyridyl boronic acid (1.84 mmol), Pd2(dba)3 (37 mg, 0.04 mmol), (t-Bu)3P (8 mg, 0.04 mmol) and Cs2CO3 (600 mg, 1.84 mmol) in dioxane (6 mL) is degassed. The mixture is then heated at 100° C. for 6 hours. The solvent is removed in vacuo and water (10 mL) and EtOAc (15 mL) is added. The layers are separated and the aqueous layer is extracted with EtOAc (15 mL). The combined extracts are washed with brine (20 mL), dried (Na2SO4), and evaporated. Preparative TLC purification of the residue provides the title product. 1H NMR (CDCl3) 8.95 (s, 1H), 8.69 (s, 2H), 8.24 (d, 1H), 7.79 (d, 1H), 7.51 (t, 1H), 7.40-7.43 (m, 1H), 7.32 (s, 1H), 7.21-7.25 (m, 1H), 7.19 (s, 1H), 5.91 (s, 2H), 2.65-2.69 (m, 2H), 1.41-1.47 (m, 2H), 0.81 (t, 3H).

Workup

  1. customis degassed
  2. customThe solvent is removed in vacuo and water (10 mL) and EtOAc (15 mL)
  3. additionis added
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with EtOAc (15 mL)
  6. washThe combined extracts are washed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customPreparative TLC purification of the residue

Sources & evidence

ORD record
ord-a9be3b2fbd4445f8b0a87495b8a7e909
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06951864B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes