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

HRID 1422995Notes

Reaction equation

HRID 1422995 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([CH2:25][N+:26]#[C-:27])(=O)=O)=CC=1>C1COCC1>[CH2:3]([N:7]1[C:12]2=[CH:25][NH:26][CH:27]=[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 161915Tosylmethyl isocyanideHCID 674157251-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 674156251-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (95%, 1.74 g, 69 mmol) is suspended in 20 mL of anhydrous THF, and then a mixture of 1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione (approx. 23 mmol) and p-toluenesulfonylmethyl isocyanide (97%, 7.0 g, 35 mmol) in 20 mL of anhydrous THF is added dropwise over 80 minutes at 0° C. The mixture is stirred at room temperature for an hour after the completion of the addition, and then carefully quenched with water. The mixture is diluted with 50 mL of 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 to give product as light brown solids, which is used for the next reaction without further purification. MS (ESI) m/z 222.2 [M+H]+.

Workup

  1. additionis added dropwise over 80 minutes at 0° C
  2. additionafter the completion of the addition
  3. customcarefully quenched with water
  4. additionThe mixture is diluted with 50 mL of 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. customto give product as light brown solids, which
  11. customis used for the next reaction without further purification

Sources & evidence

ORD record
ord-ca4a06b203f14ad1be0769ffece27111
Source dataset
uspto-grants-2015_01
Patent number
US08927556B2

Reaction notes

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