Tert-Butylamine → HCID 86692260, compound

HRID 1469782Notes

Reaction equation

HRID 1469782 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16]>N1C=CC=CC=1>[C:15]([NH:19][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 114584714-Chloro-8-nitroquinazoline

Product 1

HCID 86692260HCID 86692260, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-chloro-8-nitroquinazoline (Intermediate-7, step-2, 500 mg, 2.39 mmol), and tert-butylamine (350 mg, 4.78 mmol) in pyridine (5 mL) was stirred at rt for 3 h. Then the reaction mixture was concentrated and the residue was dissolved in EtOAc. Then the solution was washed with water and brine, separated, dried, filtered, concentrated and purified by column chromatography to afford 300 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.67 (d, J=8.4 Hz, 1H), 8.53 (s, 1H), 8.22 (d, J=7.8 Hz, 1H), 7.74 (s, 1H), 7.63-7.58 (t, J=8.0 Hz, 1H), 1.54 (s, 9H); MS [M+H]+: 247.18.

Workup

  1. concentrationThen the reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThen the solution was washed with water and brine
  4. customseparated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-09f3f88a6c4243798b9164b5f0d42cb2
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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