HCID 66551175, compound → HCID 68291086, compound

HRID 538248Notes

Reaction equation

HRID 538248 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11]3=[N:14][C:15]([CH2:17][O:18][C:19]4[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=4)=[CH:16][N:10]3[C:9]2=[O:26])=[CH:4][CH:3]=1>[Ni].CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11]3=[N:14][C:15]([CH2:17][O:18][C:19]4[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=4)=[CH:16][N:10]3[C:9]2=[O:26])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66551175HCID 66551175, compound

Product 1

HCID 68291086HCID 68291086, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Activated Raney nickel (a portion of spatula) was added to a suspension of 6-(4-fluoro-phenyl)-2-m-tolyloxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (70 mg, 0.2 mmol) in MeOH (20 mL). The mixture was hydrogenated at RT under H2 atmosphere for 3 days. The mixture was filtered through a pad of diatomaceous earth and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM with a gradient of 50/50 to 75/25). The desired fractions were collected and the solvents evaporated in vacuo to yield 6-(4-fluoro-phenyl)-2-m-tolyloxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one (34 mg, 48% yield). 1H NMR (500 MHz, CDCl3) δ ppm 2.33 (s, 3H), 3.29 (t, J=6.6 Hz, 2H), 4.00 (t, J=6.6 Hz, 2H), 5.01 (s, 2H), 6.76-6.88 (m, 3H), 7.09-7.21 (m, 3H), 7.28-7.36 (m, 2H), 7.56 (s, 1H).

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. customthe solvents were evaporated in vacuo
  3. customThe crude product was purified by flash column chromatography (silica
  4. customThe desired fractions were collected
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-b5435ee339fd458fb145a76e0a711f0a
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

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