Stannous chloride dihydrate → N4-(3-ethynylphenyl)-7-fluoroquinazoline-4,6-diamine

HRID 1968651Notes

Reaction equation

HRID 1968651 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([F:23])=[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][C:16]([F:23])=[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 59142759N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine

Product 1

HCID 59142793N4-(3-ethynylphenyl)-7-fluoroquinazoline-4,6-diamineYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine (310 mg, 1 mmol) and SnCl2.2H2O (171 mg, 4.5 mmol) in ethyl acetate (35 mL) was 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 organic layers were washed with saturated brine and H2O and dried. The solvent was removed under reduced pressure to give 225 mg (81%) N4-(3-ethynylphenyl)-7-fluoroquinazoline-4,6-diamine as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-8afe921d6fa94130af9fdd1d04ad8c16
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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