HCID 58181927, compound → HCID 58181639, compound

HRID 237318Notes

Reaction equation

HRID 237318 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O>C1COCC1.CO.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[N:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 58181927HCID 58181927, compound

Product 1

HCID 58181639HCID 58181639, compoundYield 71.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 600 mg of tert-butyl 7-nitroquinazolin-4-ylcarbamate and 150 mg of 10% Pd—C in 15 ml each of THF and MeOH was stirred overnight under a hydrogen balloon, filtered through a Celite® pad, concentrated and purified by chromatography eluting with 5% methanol in dichloromethane to provide 385 mg of tert-butyl 7-aminoquinazolin-4-ylcarbamate (Compound 98-4). MS m/e=261.1 (MH+)

Workup

  1. filtrationfiltered through a Celite® pad
  2. concentrationconcentrated
  3. custompurified by chromatography
  4. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-52626e5cea0f485e9641fcc65338003d
Source dataset
uspto-grants-2014_02
Patent number
US08642582B2

Reaction notes

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