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Ethanol → (R)-N4-(3-Chloro-4-fluorophenyl)-7-((tetrahydrofuran-3-yl)oxy)quinazoline-4,6-diamine

HRID 1744838
Notes
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Reaction equation

HRID 1744838 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][C@@H:24]4[CH2:28][CH2:27][O:26][CH2:25]4)=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(O)C.O>[Fe].C(O)(=O)C>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:23][C@@H:24]1[CH2:28][CH2:27][O:26][CH2:25]1)[N:13]=[CH:12][N:11]=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 66936816(R)-N-(3-Chloro-4-fluorophenyl)-6-nitro-7-((tetrahydrofuran-3-yl)oxy)quinazolin-4-amine

Product 1

HCID 66936486(R)-N4-(3-Chloro-4-fluorophenyl)-7-((tetrahydrofuran-3-yl)oxy)quinazoline-4,6-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst
HCID 176
Acetic Acid
Solvent

Procedure

A mixture of 12.80 g of 4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-7-((R)-tetrahydrofuran-3-yloxy)quinazoline, 200 ml of ethanol, 100 ml of water, and 17.20 ml of glacial acetic acid is heated to reflux temperature. Then a total of 7.00 g of iron powder is added in batches. The reaction mixture is refluxed for about four hours and then cooled to ambient temperature overnight. For working up, the reaction mixture is evaporated using the rotary evaporator. The residue is taken up in methylene chloride/methanol (9:1), mixed with 20 ml of concentrated ammonia solution and filtered through a layer of silica gel. It is washed with copious amounts of methylene chloride/methanol (9:1) and the combined filtrates are evaporated down. The residue is stirred with diethylether and suction filtered. Yield: 8.59 g (73% of theory); mass spectrum (ESI−): m/z=373, 375 [M−H]−; Rf value: 0.27 (silica gel, ethyl acetate/methanol=9:1).

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature
  3. temperatureThe reaction mixture is refluxed for about four hours
  4. customthe reaction mixture is evaporated
  5. customthe rotary evaporator
  6. additionmixed with 20 ml of concentrated ammonia solution
  7. filtrationfiltered through a layer of silica gel
  8. washIt is washed with copious amounts of methylene chloride/methanol (9:1)
  9. customthe combined filtrates are evaporated down
  10. filtrationfiltered

Sources & evidence

ORD record
ord-b2efe5214d3343c988073c9134c7e923
Source dataset
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07019012B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes