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

HRID 1968638Notes

Reaction equation

HRID 1968638 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. The pH was adjusted to 9-10 by treatment with 5% aqueous NaHCO3. The mixture was subjected 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 give 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 subjected 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-564de7719fb44e55b0475ea87ea9d102
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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