7-bromo-9-fluoro-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione → HCID 58118549, compound

HRID 1182830Notes

Reaction equation

HRID 1182830 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](F)[C:5]2[C:6]3[NH:14][C:13](=[O:15])[NH:12][C:11](=[O:16])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[O:18]([CH3:20])[K]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:18][CH3:20])[C:5]2[C:6]3[NH:14][C:13](=[O:15])[NH:12][C:11](=[O:16])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 581185247-bromo-9-fluoro-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dioneHCID 178502595HCID 178502595, compound

Product 1

HCID 58118549HCID 58118549, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.7 g (5.7 mmol) 7-bromo-9-fluoro-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione, 4.5 g (17.0 mmol) 18-Krone-6 and 12 ml (162.5 mmol) 30% KOMe solution (MeOH) were refluxed in 600 ml dioxan for 20 h. Having cooled down to room temperature, the solvent was concentrated, water was added and acidified using 1 N HCl. The resulting precipitate was sucked off and washed with water. 650 mg (37%) 7-bromo-9-methoxy-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione was obtained. ESI-MS [m/z]: 308, 310 [M−H]−

Workup

  1. concentrationthe solvent was concentrated
  2. additionwater was added
  3. washwashed with water

Sources & evidence

ORD record
ord-2e30b8cc74674eb9a945554184c97ee8
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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