Acetic Acid → 1-methyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1943824Notes

Reaction equation

HRID 1943824 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8](CC=C)[CH:7]=[N:6][C:5]=2[N:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]1=[O:20].C1([SiH3])C=CC=CC=1.C(O)(=O)C>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]1=[O:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 12752PhenylsilaneHCID 592995971-methyl-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 248477161-methyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

1-methyl-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.45 g, 1.63 mmol), phenylsilane (0.25 ml, 2.03 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.35 g, 0.3 mmol) was dissolved in DCM (10 ml) containing acetic acid (6 ml). The air in the flask was replaced by nitrogen by evacuating the flask then filling with nitrogen (×3) and the reaction mixture heated to 45 C for 4 h. The solution was allowed to cool diluted with DCM then washed with water then saturated sodium bicarbonate solution. The organics were isolated, dried and concentrated to yield crude product. Purification by SPE (silica) eluting with ether provided the product, 0.06 g, 16%. m/z 237 [MH+].

Workup

  1. customby evacuating the flask
  2. temperaturethe reaction mixture heated to 45 C for 4 h
  3. temperatureto cool
  4. additiondiluted with DCM
  5. washthen washed with water
  6. customThe organics were isolated
  7. customdried
  8. concentrationconcentrated
  9. customto yield crude product
  10. customPurification by SPE (silica)
  11. washeluting with ether
  12. customprovided the product, 0.06 g, 16%

Sources & evidence

ORD record
ord-d1267c85f4c44583b7942d11306abf53
Source dataset
uspto-grants-2013_03
Patent number
US08394808B2

Reaction notes

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