Diethyl Ether → HCID 90966862, compound

HRID 1867459Notes

Reaction equation

HRID 1867459 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([N:12]1[C:17](=[O:18])[C:16]2[CH:19]=[CH:20][N:21]=[CH:22][C:15]=2[N:14]=[C:13]1[CH:23](Br)[CH:24]([CH3:26])[CH3:25])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCOCC>CN(C=O)C>[N:1]([CH:23]([C:13]1[N:12]([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:17](=[O:18])[C:16]2[CH:19]=[CH:20][N:21]=[CH:22][C:15]=2[N:14]=1)[CH:24]([CH3:26])[CH3:25])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 69002008HCID 69002008, compound

Product 1

HCID 90966862HCID 90966862, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of sodium azide (1.41 g, 21.7 mmol) in DMF (12 mL) was added 3-benzyl-2-(1-bromo-2-methylpropyl)pyrido[3,4-d]pyrimidin-4(3H)-one (5.4 g, 14.50 mmol) in DMF (12 mL). The reaction was heated to 65° C. for 1.5 h, and then the solution was cooled to room temperature. The reaction contents were poured into a separatory funnel filled with ether and ice water. The organic solution was washed with brine and dried over sodium sulfate. Filtration and concentration afforded the title compound as a brown oil. 1H NMR (500 MHz, CDCl3) δ 0.61 (d, J=6.5 Hz, 3H), 1.09 (d, J=6.5 Hz, 3H), 2.67-2.73 (m, 1H), 3.71 (d, J=10 Hz, 1H), 5.10 (d, J=16.5 Hz, 1H), 5.83 (d, J=16 Hz, 1H), 7.16 (d, J=8 Hz, 2H), 7.32-7.38 (m, 3H), 8.12 (d, J=6.5 Hz, 1H), 8.75 (d, J=5.5 Hz, 1H), 9.13 (s, 1H). MS [M+H] C18H18N6O=335.1.

Workup

  1. temperaturethe solution was cooled to room temperature
  2. customThe reaction contents
  3. additionwere poured into a separatory funnel
  4. washThe organic solution was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-a19eaa6f5a5140a4a5e99bf10c5bf44e
Source dataset
uspto-grants-2009_12
Patent number
US07632839B2

Reaction notes

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