N-methyl-2-pyrrolidone → HCID 11962224, compound

HRID 1805864Notes

Reaction equation

HRID 1805864 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:18]2[C:17]([O:19][C:20]3[C:27]([CH3:28])=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=3[CH3:29])=[N:16][C:15](F)=[N:14][C:13]=2[CH:12]=[CH:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C[N:32]1[C:36](=O)[CH2:35][CH2:34][CH2:33]1>O>[CH2:3]([N:10]1[C:18]2[C:17]([O:19][C:20]3[C:27]([CH3:28])=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=3[CH3:29])=[N:16][C:15]([NH:10][C:3]3[CH:33]=[CH:34][C:35]([C:36]#[N:32])=[CH:5][CH:4]=3)=[N:14][C:13]=2[CH:12]=[CH:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidone2×HCID 24758Sodium hydrideHCID 57693621HCID 57693621, compound

Product 1

HCID 11962224HCID 11962224, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of NaH (101 mg, 4.21 mmol) in dry NMP (4 mL) was added 4-aminobenzylnitrile (299 mg, 2.53 mmol) and stirred at room temperature for 30 min under argon. The reaction mixture was added to a solution of 4-(5-benzyl-2-fluoro-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile (314 mg, 0.84 mmol) in dry NMP (4.4 mL) and stirred at room temperature for 2 h. After completion of the reaction, the resulting mixture was diluted with water and washed with EtOAc×3. The combined organic layers were washed with water, NH4Cl, water×2, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography, eluting with 1% MeOH:CH2Cl2, producing the product as a tan solid (320 mg, 80%).

Workup

  1. stirringstirred at room temperature for 2 h
  2. customAfter completion of the reaction
  3. washwashed with EtOAc×3
  4. washThe combined organic layers were washed with water, NH4Cl, water×2, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography
  9. washeluting with 1% MeOH

Sources & evidence

ORD record
ord-bbd246c1d14843aaa1fe223eccce15db
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

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