Dimethylformamide → HCID 18326471, compound

HRID 1250591Notes

Reaction equation

HRID 1250591 reaction equation
[CH2:1]([NH:4][C:5]1[N:14]=[C:13]([NH2:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=2)[N:6]=1)[CH:2]=[CH2:3].[CH3:19][C:20]([CH3:23])([O-])[CH3:21].[K+].[C:25]([N:29]=[C:30]=[O:31])([CH3:28])([CH3:27])[CH3:26].C[N:33]([CH:35]=[O:36])C>>[CH2:1]([N:4]([C:5]1[N:14]=[C:13]([NH:15][C:30](=[O:31])[NH:29][C:25]([CH3:28])([CH3:27])[CH3:26])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=2)[N:6]=1)[C:35](=[O:36])[NH:33][C:20]([CH3:23])([CH3:21])[CH3:19])[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 62412tert-Butyl isocyanateHCID 183264362-Allylamino-4-amino-6-nitroquinazolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 18326471HCID 18326471, compoundYield 36%

Conditions

Temperature
150 °C

Procedure

To 5 ml of a solution of 123 mg (0.50 mmol) of 2-allylamino-4-amino-6-nitroquinazoline in DMF were added 56 mg (0.55 mmol) of potassium t-butoxide and 50 mg (0.50 mmol) of t-butylisocyanate, and then the reaction mixture was subjected to heating at 150° C. for 0.5 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified by a silica gel chromatography to give 80 mg (yield: 36.0%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-ee6629e5e88e42a282eb4c45571feec1
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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