Dimethylformamide → HCID 59299535, compound

HRID 2386622Notes

Reaction equation

HRID 2386622 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].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:31][N:32](C=O)C>C1COCC1>[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[NH:8][C:7]([C:31]#[N:32])=[N:6][C:5]=2[N:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]1=[O:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2733832Lithium HexamethyldisilazideHCID 592995971-methyl-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 59299535HCID 59299535, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-methyl-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (1.05 g, 3.6 mmol) in THF (15 ml) at −78° C. was added LiHMDS (4 ml, 1M in hexane, 4 mmol) over 10 min and the solution stirred for 0.5 h. DMF (0.5 ml) was added and the solution stirred at −78° C. for a further 0.5 h then allowed to warm to ambient temperature with the cooling bath over 2 h. The reaction was quenched with 2N hydrochloric acid (3 ml) and partioned between ethyl acetate and brine. The organics were isolated, dried and concentrated. The crude product was chromatographed over silica (gradient elution dichloromethane to 5:1 dichloromethane/ethyl acetate) to afford the title compound as a white solid (0.35 g, 30%). m/z 305 [MH+]

Workup

  1. stirringthe solution stirred at −78° C. for a further 0.5 h
  2. customThe reaction was quenched with 2N hydrochloric acid (3 ml)
  3. customThe organics were isolated
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was chromatographed over silica (gradient elution dichloromethane to 5:1 dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-895c8772b4ab41b1b4c7fd97355b90b2
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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