Ammonium Hydroxide → HCID 69708897, compound

HRID 2183923Notes

Reaction equation

HRID 2183923 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[N+:21]([O-])=O.[Sn](Cl)Cl.[OH-].[NH4+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([F:19])([F:20])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[NH2:21]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24479Stannous ChlorideHCID 69708338HCID 69708338, compound

Product 1

HCID 69708897HCID 69708897, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3-(4-fluoro-3-nitrophenyl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (0.819 g, 2.51 mmol) in ethanol (10 ml) was added anhydrous tin(II) chloride (2.0 g). After stirring at ambient temperature for 2 h the resulting solution was treated with 30% ammonium hydroxide (40 ml). This mixture was stirred for 10 min then concentrated at reduced pressure. The residue was then treated with ethanol and evaporated at reduced pressure to remove residual water. This residue was then boiled with 10% methanol in dichloromethane and insoluble material removed by filtration. The filtrate was evaporated in vacuo, the residue treated with a hot solution of 50% toluene in ethyl acetate and insoluble material removed by filtration. The filtrate was evaporated at reduced pressure and the residue crystallised from hot toluene to furnish 2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenylamine: δH (400 MHz, DMSO) 5.42 (2H, br), 6.87 (1H, m), 7.07 (1H, dd, J 9 and 2), 7.20 (1H, dd, J 12 and 8), 7.50 (1H, d, J 7), 8.13 (1H, s), 9.18 (1H, d, J 7); m/z (ES+) 297 (M++H).

Workup

  1. stirringThis mixture was stirred for 10 min
  2. concentrationthen concentrated at reduced pressure
  3. additionThe residue was then treated with ethanol
  4. customevaporated at reduced pressure
  5. customto remove residual water
  6. customremoved by filtration
  7. customThe filtrate was evaporated in vacuo
  8. additionthe residue treated with a hot solution of 50% toluene in ethyl acetate and insoluble material
  9. customremoved by filtration
  10. customThe filtrate was evaporated at reduced pressure
  11. customthe residue crystallised from hot toluene

Sources & evidence

ORD record
ord-e2a9609f46f048c896d8a1c7f6ac8f74
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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