Sodium hydride → 1-isobutyl-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2205659Notes

Reaction equation

HRID 2205659 reaction equation
[H-].[Na+].[CH2:3]([N:7]1[CH:12]=[CH:11][C:10](=[O:13])[N:9]([CH3:14])[C:8]1=[O:15])[CH:4]([CH3:6])[CH3:5].C1(C)C=CC(S([CH:25]([N+:27]#[C-:28])[CH3:26])(=O)=O)=CC=1>C1COCC1>[CH2:3]([N:7]1[C:12]2=[C:25]([CH3:26])[NH:27][CH:28]=[C:11]2[C:10](=[O:13])[N:9]([CH3:14])[C:8]1=[O:15])[CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzeneHCID 674157251-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 674148801-isobutyl-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (95%, 116 mg, 4.6 mmol) is suspended in 10 mL of anhydrous THF, and then a mixture of 1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione (300 mg, 1.65 mmol) and 1-(p-toluenesulfonyl)-ethyl isocyanide (413 mg, 1.98 mmol) in 5 mL of anhydrous THF is added dropwise over 1 h at 0° C. The mixture is stirred at room temperature for 3 h at room temperature after the completion of the addition, and then carefully quenched with water. The mixture is diluted with saturated NaHCO3, and then extracted with CH2Cl2 five times. The combined organic phase is washed with brine, and then dried with anhydrous Na2SO4. After filtration, the filtrate is evaporated to dryness under reduced pressure, and the residue is purified by basic alumina column chromatography to give 247 mg of product (yield: 64%). MS (ESI) m/z 236.1 [M+H]+.

Workup

  1. additionis added dropwise over 1 h at 0° C
  2. additionafter the completion of the addition
  3. customcarefully quenched with water
  4. additionThe mixture is diluted with saturated NaHCO3
  5. extractionextracted with CH2Cl2 five times
  6. washThe combined organic phase is washed with brine
  7. dry with materialdried with anhydrous Na2SO4
  8. filtrationAfter filtration
  9. customthe filtrate is evaporated to dryness under reduced pressure
  10. customthe residue is purified by basic alumina column chromatography

Sources & evidence

ORD record
ord-6cb0a117cbdb41549b7af97e4ffa5c8a
Source dataset
uspto-grants-2016_06
Patent number
US09371327B2

Reaction notes

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