Dimethylformamide → 5-Allyl-3-methyl-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one

HRID 244459Notes

Reaction equation

HRID 244459 reaction equation
[CH2:1]([N:4]1[C:12]2C(Cl)=NC=[N:8][C:7]=2[CH:6]=[CH:5]1)[CH:2]=[CH2:3].[H-].[Na+].CI.[CH3:18][N:19]([CH:21]=[O:22])[CH3:20]>O>[CH2:1]([N:4]1[C:12]2[C:21](=[O:22])[N:19]([CH3:20])[CH:18]=[N:8][C:7]=2[CH:6]=[CH:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 594373215-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 594372775-Allyl-3-methyl-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-oneYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a room temperature solution of 5-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine (220 mg, 1.3 mmol, 1 equiv.) in 3 mL of DMF was added 60% NaH (100 mg, 2.5 mmol, 2 equiv.) followed by MeI (0.18 ml, 1.8 mmol, 1.5 equiv.). After 30 minutes, the mixture was diluted with water and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by reverse phase HPLC (5-90% CH3CN/water+0.1% TFA). The desired fractions were combined and concentrated to remove CH3CN. The remaining aqueous mixture was extracted with EtOAc, dried, filtered, and evaporated to provide 152 mg (64%) of 5-allyl-3-methyl-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one as a yellow oil which was used without further purification.

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by reverse phase HPLC (5-90% CH3CN/water+0.1% TFA)
  6. concentrationconcentrated
  7. customto remove CH3CN
  8. extractionThe remaining aqueous mixture was extracted with EtOAc
  9. customdried
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-7b18bbcdd92f4a0c9ff57180fd1089fb
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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