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

HRID 965687Notes

Reaction equation

HRID 965687 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]=[C:4]([CH3:24])[N:3]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.[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])=[CH:2][N:3]=[C:4]([CH3:24])[N:5]=3)[CH:16]=[CH:15][N:14]=2)=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 99977004-Chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-methyl-5-propyl-pyrimidine

Product 1

HCID 223131584-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-methyl-5-propyl-pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-methyl-5-propyl-pyrimidine (55.3 mg, 0.16 mmol), K2CO3 (30 mg) and Pd—C (10%, 6 mg) in ethanol is stirred at room temperature under H2 (H2 balloon) over night. After filtration, the solvent is removed and the residue is purified by preparative TLC to give the title compound. 1H NMR (CDCl3) 8.34 (s, 1H), 8.31-8.33 (m, 1H), 7.50-7.55 (m, 1H), 7.23-7.28 (m, 2H), 7.10 (s, 1H), 5.73 (s, 2H), 2.54 (s, 3H), 2.48 (t, 2H), 1.44-1.53 (m, 2H), 0.89 (t, 3H).

Workup

  1. filtrationAfter filtration
  2. customthe solvent is removed
  3. customthe residue is purified by preparative TLC

Sources & evidence

ORD record
ord-e9dc5277bea043f58aabcb132b1727f5
Source dataset
uspto-grants-2005_10
Patent number
US06951864B2

Reaction notes

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