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

HRID 1463348ノート

反応式

HRID 1463348 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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 (pH8) 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) δ8.32 (s, 1H), 7.87 (s, 1H), 4.83-4.68 (m, 1H), 4.26-4.19 (m, 1 H), 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).

後処理

  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

出典と根拠

ORDレコード
ord-273554b6dac043cc8d0508eda694d477
出典データセット
uspto-grants-1994_04
特許番号
US05300506

反応ノート

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