Trifluoroacetic acid → 1-(5-Methoxy-4-pyrimidinyl)-2-methylpiperazine

HRID 1647800Notes

Reaction equation

HRID 1647800 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([O:20][CH3:21])=[CH:18][N:17]=[CH:16][N:15]=2)[CH:10]([CH3:22])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CCOCC>[CH3:21][O:20][C:19]1[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]2[CH3:22])=[N:15][CH:16]=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 199216611-(t-Butoxycarbonyl)-4-(5-methoxy-4-pyrimidinyl)-3-methylpiperazine

Product 1

HCID 190814741-(5-Methoxy-4-pyrimidinyl)-2-methylpiperazineYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(t-butoxycarbonyl)-4-(5-methoxy-4-pyrimidinyl)-3-methylpiperazine (1.70 g, 4.2 mmol) and trifluoroacetic acid (5 mL) in 50 mL of CH2Cl2 was stirred at r.t. under Ar for 18 h. The solution was evaporated, the residue was taken up in water and the mixture was basified (pHS) with 15% aqueous NaOH. The resulting (pH 8) mixture was extracted with ethyl acetate and the organic phase was washed (H2O, brine), dried (Na2SO4) and evaporated to give a semi-solid. This material was taken up in ether, filtered to remove insoluble material and the solution was evaporated to give the product (0.80 g, 92%) as an oil. It was used without further purification: IR (neat) 3300, 1580, 1540 cm-1 ; 1H nmr (200 MHz, CDCl3) δ 8.32 (S, 1H), 7.87 (s, 1H), 4.83-4.68 (m, 1H), 4.26-4.19 (m, 1H), 3.85 (s, 3H), 3.26-3.17 (m, 1H), 3.12-3.01 (m, 2H), 2.94-2.80 (m, 2H), 1.29 (d, J=6.8 Hz, 3H) .

Workup

  1. customThe solution was evaporated
  2. extractionThe resulting (pH 8) mixture was extracted with ethyl acetate
  3. washthe organic phase was washed (H2O, brine)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a semi-solid
  7. filtrationfiltered
  8. customto remove insoluble material
  9. customthe solution was evaporated

Sources & evidence

ORD record
ord-f9815f3289a34a398f3fa53c32ea02e3
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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