2,4-Dimethoxybenzylamine → N-(6-Amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

HRID 2069196Notes

Reaction equation

HRID 2069196 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]2=[O:21].COC1C=C(OC)C=CC=1C[NH2:27]>C(O)C>[NH2:27][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]2=[O:21]

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 58964482N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11674068N-(6-Amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the yellow solution of N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (500 mg, 1.57 mmol) in ethanol (0.5 ml) is added 2,4-dimethoxybenzylamine (4.72 ml, 31.4 mmol) under argon. The solution is heated at 150° in a closed vial in a microwave reactor for 4 minutes. After removal of the solvent and 2,4-dimethoxybenzylamine by high-vacuum rotavapor evaporation the remaining deep purple oil is treated with diethyl ether to obtain a suspension, which is filtered and dried to yield the crude title compound as a deep purple solid, m.p. 232-237° C.

Workup

  1. temperatureThe solution is heated at 150° in a closed vial in a microwave reactor for 4 minutes
  2. customAfter removal of the solvent and 2,4-dimethoxybenzylamine
  3. customby high-vacuum rotavapor evaporation the remaining deep purple oil
  4. additionis treated with diethyl ether
  5. customto obtain a suspension, which
  6. filtrationis filtered
  7. customdried

Sources & evidence

ORD record
ord-073f837e9a704627adc57db4d4e1bce2
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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