Dimethylformamide → 1-Methyl-2,6-dioxo-3-pentyl-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbaldehyde

HRID 2234937Notes

Reaction equation

HRID 2234937 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8]([CH2:12][CH:13]=[CH2:14])[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.CN([CH:34]=[O:35])C>C1COCC1>[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8]([CH2:12][CH:13]=[CH2:14])[C:7]([CH:34]=[O:35])=[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 592995531-Methyl-2,6-dioxo-3-pentyl-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbaldehydeYield 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 chomatographed 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

Sources & evidence

ORD record
ord-e54e7a97abf549f1bb51538fe52aed25
Source dataset
uspto-grants-2010_05
Patent number
US07713982B2

Reaction notes

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