Stannous chloride dihydrate → N4-(3-Ethynylphenyl)quinazoline-4,6-diamine

HRID 1968625Notes

Reaction equation

HRID 1968625 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 16045443N-(3-ethynylphenyl)-6-nitroquinazolin-4-amine

Product 1

HCID 11492625N4-(3-Ethynylphenyl)quinazoline-4,6-diamineYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(3-ethynylphenyl)-6-nitroquinazolin-4-amine (1.00 g, 3.45 mmol) and SnCl2.2H2O (3.10 g, 13.8 mmol) in ethyl acetate (35 mL) was refluxed for 2 h and then cooled to room temperature. After its pH was adjusted to 9-10 with 5% aqueous NaHCO3, the mixture was subject to extraction with EtOAc. The combined organic layers were washed with saturated brine and H2O and dried. The solvent was removed under reduced pressure to provide 0.79 g (89%) of N4-(3-ethynylphenyl)quinazoline-4,6-diamine as a yellow solid.

Workup

  1. temperaturewas refluxed for 2 h
  2. extractionthe mixture was subject to extraction with EtOAc
  3. washThe combined organic layers were washed with saturated brine and H2O
  4. customdried
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b9d9d20b922948a08f574aebd9269fff
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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