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

HRID 1647800

반응식

HRID 1647800 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

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) .

후처리

  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

출처 및 근거

ORD 기록
ord-f9815f3289a34a398f3fa53c32ea02e3
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05434154

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