HCID 135813645, compound → HCID 135813641, compound

HRID 1760748Notes

Reaction equation

HRID 1760748 reaction equation
[CH3:1][NH:2][C:3]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:16])[NH:6][CH:7]=[N:8]2>CO.[Pt]=O>[NH2:13][C:12]1[C:3]([NH:2][CH3:1])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=[O:16]

Participants

4

Reactant 1

HCID 135813645HCID 135813645, compound

Product 1

HCID 135813641HCID 135813641, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

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. filtrationThe mixture was filtered through diatomaceous earth
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-1f3937968ada44f8bced478f6699b010
Source dataset
uspto-grants-2005_01
Patent number
US06844435B2

Reaction notes

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