Potassium Carbonate → tert-Butyl 4-(4-phenyl-5-pyrimidin-4-yl-1H-imidazol-1-yl)piperidine-1-carboxylate

HRID 1896659Notes

Reaction equation

HRID 1896659 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([CH:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)S(C1C=CC(C)=CC=1)(=O)=O)#[C-:8].[N:26]1[CH:31]=[CH:30][C:29](/[CH:32]=[N:33]/[CH:34]2[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]2)=[N:28][CH:27]=1>CN(C=O)C.[OH-].[Na+]>[C:20]1([C:9]2[N:7]=[CH:8][N:33]([CH:34]3[CH2:35][CH2:36][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:38][CH2:39]3)[C:32]=2[C:29]2[CH:30]=[CH:31][N:26]=[CH:27][N:28]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10967613a-Tosylbenzyl isocyanideHCID 178452095HCID 178452095, compound

Product 1

HCID 58235125tert-Butyl 4-(4-phenyl-5-pyrimidin-4-yl-1H-imidazol-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of potassium carbonate (107 mg, 0.774 mmol), 1-{[isocyano(phenyl)methyl]sulfonyl}-4-methylbenzene (C21, see Organic Syntheses; Wiley & Sons: New York, 2004; Collect. Vol. 10, p. 692) (0.209 g, 0.770 mmol) and tert-butyl 4-{[(1E)-pyrimidin-4-ylmethylene]amino}piperidine-1-carboxylate (C13) (582 mg, 2.00 mmol) in DMF (3 mL) was stirred for 18 hours at room temperature, then diluted with aqueous sodium hydroxide solution (1 N, 50 mL). The mixture was extracted with ethyl acetate, and the combined organic layers were washed with aqueous lithium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Eluants: 50%, then 75% ethyl acetate in heptane) provided the product as a cream-colored solid. Yield: 267 mg, 0.658 mmol, 85%. APCI m/z 406.0 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.49 (s, 9H), 1.82-1.92 (m, 2H), 2.17 (br d, J=12 Hz, 2H), 2.77-2.86 (m, 2H), 4.26-4.34 (m, 2H), 4.93 (tt, J=12, 4 Hz, 1H), 7.20 (dd, J=5.3, 1.5 Hz, 1H), 7.32-7.36 (m, 3H), 7.42-7.45 (m, 2H), 7.80 (s, 1H), 8.54 (d, J=5.3 Hz, 1H), 9.28 (d, J=1.3 Hz, 1H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe combined organic layers were washed with aqueous lithium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography (Eluants

Sources & evidence

ORD record
ord-afac969710454af3b6d7664660e88be0
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

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