Acetonitrile → HCID 57672267, compound

HRID 252069Notes

Reaction equation

HRID 252069 reaction equation
Cl[CH2:2][C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[CH:9]1([CH2:15][N:16]2[CH2:24][C:23]3[C:18](=[C:19]([CH3:32])[CH:20]=[C:21]([CH2:25][CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH:22]=3)[C:17]2=[O:33])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>O>[CH:9]1([CH2:15][N:16]2[CH2:24][C:23]3[C:18](=[C:19]([CH3:32])[CH:20]=[C:21]([CH2:25][CH:26]4[CH2:27][CH2:28][N:29]([CH2:2][C:3]5[N:8]=[CH:7][CH:6]=[CH:5][N:4]=5)[CH2:30][CH2:31]4)[CH:22]=3)[C:17]2=[O:33])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 128773712-(Chloromethyl)pyrimidineHCID 57672262HCID 57672262, compound

Product 1

HCID 57672267HCID 57672267, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-Chloromethylpyrimidine (32 mg, 0.247 mmol), 2-Cyclohexylmethyl-7-methyl-5-piperidin-4-ylmethyl-2,3-dihydro-isoindol-1-one (56 mg, 0.164 mmol) and cesium carbonate (160 mg, 0.492 mmol) was added acetonitrile (3.0 mL). The mixture was allowed to stir at room temperature overnight. Water (2.0 mL) was added and the product was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. Column chromatography provided the title compound as a yellow oil (48 mg, 69%). 1H NMR (300 Adz, CDCl3): δ 8.76-8.72 (d, 2H), 7.18 (t, 1H), 6.99 (s, 1H), 6.95 (s, 1H), 4.30 (s, 2H), 3.78 (s, 2H), 3.40-3.37 (d, 2H), 2.97-2.93 (d, 2H), 2.70 (s, 3H), 2.58-2.56 (d, 2H), 2.10-2.05 (t, 2H), 1.71-1.42 (m, 10H), 1.26-1.13 (m, 4H), 1.09-0.98 (m, 2H).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a37101059361465eae0622156d65d6a0
Source dataset
uspto-grants-2011_01
Patent number
US07868008B2

Reaction notes

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