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

HRID 1968641Notes

Reaction equation

HRID 1968641 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

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) were refluxed for 2 h. After cooled to room temperature, the mixture was treated with 5% aqueous NaHCO3 to adjust its pH to 9-10 and then subjected to extraction with EtOAc. The combined organic layers were washed with saturated brine and H2O, dried, and concentrated under reduced pressure to give 0.79 g (89%) of N4-(3-ethynylphenyl)quinazoline-4,6-diamine as a yellow solid.

Workup

  1. extractionsubjected to extraction with EtOAc
  2. washThe combined organic layers were washed with saturated brine and H2O
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2aae24fbcb9f43b9a6d1da031fd01484
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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