N-methyl-2-pyrrolidone → HCID 57693562, compound

HRID 1516846Notes

Reaction equation

HRID 1516846 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:18]2[C:17]([S:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])=[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:31]1[C:35](=O)[CH2:34][CH2:33][CH2:32]1>O>[CH2:3]([N:10]1[C:18]2[C:17]([S:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])=[N:16][C:15]([NH:10][C:3]3[CH:32]=[CH:33][C:34]([C:35]#[N:31])=[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 57693636HCID 57693636, compound

Product 1

HCID 57693562HCID 57693562, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of NaH (30 mg, 1.25 mmol) in dry NMP (1.5 mL) was added 4-aminobenzylnitrile (87.4 mg, 0.74 mmol) and stirred at room temperature for 30 min under argon. The reaction mixture was added to a solution of 5-benzyl-2-fluoro-4-(mesitylthio)-5H-pyrrolo[3,2-d]pyrimidine (93 mg, 0.25 mmol) in dry NMP (1 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 preparative TLC, eluting with Hexanes:Ethyl acetate (1.5:1) afforded the product as a tan solid (12.6 mg, 11%).

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 preparative TLC
  9. washeluting with Hexanes:Ethyl acetate (1.5:1)

Sources & evidence

ORD record
ord-7d098b8b9abe40828f6d069f114de91f
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Reaction notes

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