Trifluoroacetic acid → 2-(2,6-Diethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-4-methyl-6-piperazin-1-ylpyrimidine

HRID 1455759

Reaction equation

HRID 1455759 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[C:15]([N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)[C:14]([CH2:30][O:31][C:32]2[CH:37]=[C:36]([CH:38]([CH3:40])[CH3:39])[CH:35]=[CH:34][C:33]=2[CH3:41])=[C:13]([CH3:42])[N:12]=1)[CH3:2].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:11]1[N:12]=[C:13]([CH3:42])[C:14]([CH2:30][O:31][C:32]2[CH:37]=[C:36]([CH:38]([CH3:39])[CH3:40])[CH:35]=[CH:34][C:33]=2[CH3:41])=[C:15]([N:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)[N:16]=1)[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11548705Tert-butyl 4-{2-(2,6-diethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-6-methylpyrimidin-4-yl}piperazine-1-carboxylate

Product 1

HCID 575314682-(2,6-Diethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-4-methyl-6-piperazin-1-ylpyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To tert-butyl 4-{2-(2,6-diethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-6-methylpyrimidin-4-yl}piperazine-1-carboxylate (228 mg, 0.40 mmol) is added trifluoroacetic acid (2 mL). Gas evolution ensues and rapidly subsides. Toluene (10 mL) is added and removed under reduced pressure. The resulting residue is dissolved in EtOAc (25 mL) and extracted with saturated potassium carbonate (10 mL) followed by brine (10 mL), dried over sodium sulfate, filtered and evaporated at reduced pressure to obtain the title compound as a colorless oil. LC/MS (Method 3), M+H=473.2, Rt=2.35 min.; 1H NMR (CDCl3) δ=7.26 (d, 1H), 7.12 (d, 3H), 6.83 (m, 2H), 4.99 (s, 2H), 3.49 (m, 8H), 2.91 (m, 1H), 2.56, (s, 3H), 2.42 (q, 4H) 2.24 (s, 3H), 1.42 (s, 9H), 1.28 (d, 6H), 1.13 (t, 6H).

Workup

  1. customremoved under reduced pressure
  2. dissolutionThe resulting residue is dissolved in EtOAc (25 mL)
  3. extractionextracted with saturated potassium carbonate (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-ca3259491cd94cee9d0d8a6f3c387ec8
Source dataset
uspto-grants-2009_01
Patent number
US07482350B2

Linked notes

Loading…