Sodium Hydroxide → HCID 22732477, compound

HRID 1765194Notes

Reaction equation

HRID 1765194 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][C:3]=1[NH:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:8]=[C:7]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:6]=1.[Sn](Cl)(Cl)(Cl)[Cl:29].[OH-].[Na+]>C(O)C>[ClH:29].[NH2:25][C:22]1[CH:23]=[CH:24][C:2]([CH3:1])=[C:3]([CH:21]=1)[NH:4][C:5]1[CH:10]=[C:9]([C:11]([F:13])([F:14])[F:12])[N:8]=[C:7]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 99696934-(2-Methyl-5-nitroanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 22732477HCID 22732477, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(2-methyl,5-nitroanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (75 mg, 0.200 mmol) in anhydrous ethanol (10 ml) was added slowly anhydrous tin chloride (152 mg, 0.800 mmol). The mixture was refluxed for 1 h and then rotary evaporated to leave a brown oil. The brown oil was basified with 2N NaOH to give a final pH of 8. The resulting precipitate was filtered and washed with ethyl acetate. The aqueous phase and organic phase was combined, washed with water (1×20 ml) and dried over anhydrous sodium sulfate. The ethyl acetate was rotary evaporated to dryness to give a dark yellow solid (33 mg, 44%). 1H NMR (CDCl3): 9.69–9.68 (m, 1H), 8.73–8.67 (m, 2H), 7.53 (s, 1H), 7.43–7.39 (m, 1H), 7.11 (d, J=8.4 Hz, 1H), 6.72 (s, 1H), 6.64 (d, J=2.7 Hz, 1H), 6.61 (s, 1H), 3.01 (bs, 2H), 2.17 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customrotary evaporated
  3. customto leave a brown oil
  4. customto give a final pH of 8
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with ethyl acetate
  7. washwashed with water (1×20 ml)
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe ethyl acetate was rotary evaporated to dryness

Sources & evidence

ORD record
ord-6c8898e1426f4f56ab43c65816717b57
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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