Chloroacetonitrile → HCID 86698136, compound

HRID 2362325Notes

Reaction equation

HRID 2362325 reaction equation
[Cl:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[N:6]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[CH:7]=[N:8][C:9]=2[N:10]=1.[H-].[Na+].Cl[CH2:24][C:25]#[N:26]>CN(C=O)C>[Cl:1][C:2]1[N:3]([CH2:24][C:25]#[N:26])[C:4](=[O:20])[C:5]2[N:6]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[CH:7]=[N:8][C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 7856Chloroacetonitrile2×HCID 24758Sodium hydrideHCID 136378632HCID 136378632, compound

Product 1

HCID 86698136HCID 86698136, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-chloro-7-(4-methoxybenzyl)-1H-purin-6(7H)-one 7 (5.98 g, 20.62 mmol) in DMF (90 ml) at 0° C. was added NaH (1.072 g, 26.81 mmol). The mixture was stirred at room temperature for 10 minutes, and then stirred at 55° C. for 3 hours. Chloroacetonitrile (1.57 ml, 24.74 mmol) was added to the reaction flask at 0° C. The reaction mixture was stirred over night. Another 0.65 ml (10.31 mmol) of chloroacetonitrile was added into the reaction flask. The mixture was stirred over night. The reaction was quenched with water at 0° C. The mixture was extracted with DCM (3×), washed with water and brine, dried (MgSO4) and concentrated. The crude product was purified by flash chromatography (EtOAc/Hexane) to afford pure product 2-(2-chloro-7-(4-methoxybenzyl)-6-oxo-6,7-dihydro-1H-purin-1-yl)acetonitrile 8. 1H NMR δ 7.878 (s, 1H), 7.269 (d, J=8.8 Hz, 2H), 6.880, (d, J=8.8 Hz, 2H), 5.465 (s, 2H), 5.189 (s, 2H), 3.789 (s, 3H).

Workup

  1. stirringstirred at 55° C. for 3 hours
  2. stirringThe reaction mixture was stirred over night
  3. stirringThe mixture was stirred over night
  4. customThe reaction was quenched with water at 0° C
  5. extractionThe mixture was extracted with DCM (3×)
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-45da5abf7c2c4f20aba6f8a31facaf6e
Source dataset
uspto-grants-2014_04
Patent number
US08691832B2

Reaction notes

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