Sodium Hydroxide → 4-(5-Amino-2-methylanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 2084181Notes

Reaction equation

HRID 2084181 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:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[N:6]=1.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>C(O)C>[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:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 227323994-(2-Methyl-5-nitroanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 227324584-(5-Amino-2-methylanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidineYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(2-methyl,5-nitroanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine (377 mg, 1.00 mmol) in anhydrous ethanol (20 ml) was added slowly anhydrous tin chloride (758 mg, 4.00 mmol). The mixture was refluxed for 1 h and then rotary evaporated to leave a brown oil. The brown oil was basified with aqueous 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 and washed with water (1×20 ml) and dried over anhydrous sodium sulfate. The ethyl acetate solution was rotary evaporated to dryness to give a brown solid (212 mg, 57%). 1H NMR (CDCl3): 8.76 (dd, J=1.8, 4.8 Hz, 2H), 8.26 (dd, J=1.8, 4.8 Hz, 2H), 7.11 (d, J=7.8 Hz, 1H), 7.12 (s, 1H), 6.69 (d, J=2.4 Hz, 1H), 6.66 (s, 1H), 6.63 (dd, J=2.4, 8.1 Hz, 1H), 3.72 (bs, 2H), 2.16 (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 solution was rotary evaporated to dryness

Sources & evidence

ORD record
ord-533e349b8346445cb7e96feff21840f6
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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