Methylamine → HCID 135813645, compound

HRID 2296712Notes

Reaction equation

HRID 2296712 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:15])[NH:5][CH:6]=[N:7]2.[CH3:16][NH2:17]>CO>[CH3:16][NH:17][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:15])[NH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 135813639HCID 135813639, compound

Product 1

HCID 135813645HCID 135813645, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloro-6-nitroquinazolin-4-one, from Example 3 (0.26 g, 1.15 mmol) was suspended in MeOH (3 mL) at −20° C. Methylamine gas was passed into the mixture for a few minutes, resulting in a clear solution. The solution was stirred at room temperature for 5 h and evaporated to give 5-methylamino-6-nitroquinazolin-4-one in quantitative yield. The above amine (350 mg, 1.6 mmol) was hydrogenated over platinum oxide (30 mg) in MeOH (200 mL) at 60 psi for 4 h. The mixture was filtered through diatomaceous earth and the solvent evaporated, to give 6-amino-5-methylaminoquinazolin-4-one, which was immediately suspended in EtOAc (20 mL) and THF (10 mL). A solution of 2,6-dichlorophenylisothiocyanate (340 mg, 1.67 mmol) in EtOAc (5 mL) was added, and the mixture stirred for 16 h. The reaction mixture was concentrated to half the volume, filtered, and the solid washed with EtOAc to yield the thiourea (400 mg, 64% over 2 steps.)

Workup

  1. customresulting in a clear solution
  2. customevaporated

Sources & evidence

ORD record
ord-c69c28877a564f2980da2bb20318f313
Source dataset
uspto-grants-2002_12
Patent number
US06489328B2

Reaction notes

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