6-(2-nitro-5-(piperidin-1-yl)phenyl)-N-(1-(3-(trifluoromethyl)phenyl)-ethyl)pyrimidin-4-amine → HCID 66588120, compound

HRID 1408150Notes

Reaction equation

HRID 1408150 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[C:16]1[N:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[CH3:24])[CH:17]=1)([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)=[CH:6][C:5]=1[C:16]1[N:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:34])[F:33])[CH:26]=2)[CH3:24])[CH:17]=1

Participants

4

Reactant 1

HCID 665869426-(2-nitro-5-(piperidin-1-yl)phenyl)-N-(1-(3-(trifluoromethyl)phenyl)-ethyl)pyrimidin-4-amine

Product 1

HCID 66588120HCID 66588120, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Into a 100-mL round-bottom flask, was placed a solution of 6-(2-nitro-5-(piperidin-1-yl)phenyl)-N-(1-(3-(trifluoromethyl)phenyl)ethyl)pyrimidin-4-amine (400 mg, 0.85 mmol, 1.00 equiv) in acetic acid (5 mL). To this was added zinc (552 mg, 8.62 mmol, 10.00 equiv) in several batches at 70° C. The resulting solution was stirred for 1 h at 70° C. The solids were filtered out. The resulting mixture was concentrated under vacuum. The solution was adjusted to pH 8 with ammonia (1 mol/L). The resulting solution was extracted with 4×50 ml of ethyl acetate and the organic layers combined, dried over sodium sulfate, and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with methanol:dichloromethane (1:50). The product was obtained as 200 mg (53%) of a black solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. extractionThe resulting solution was extracted with 4×50 ml of ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. washeluted with methanol:dichloromethane (1:50)

Sources & evidence

ORD record
ord-2b3561161a1844cdb62dde12f58955dd
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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