Ethyl Acetate → (S)-4-(2-chloro-9-methyl-9H-purin-6-yl)-3-methylmorpholine

HRID 2063361노트

반응식

HRID 2063361 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4](Cl)[N:3]=1.[CH3:13][C@H:14]1[CH2:19][O:18][CH2:17][CH2:16][NH:15]1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>C(O)C.CN(C=O)C.C(OCC)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][C@@H:14]2[CH3:13])[N:3]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 17125532,6-dichloro-9-methyl-9H-purineHCID 12012220(3S)-3-methylmorpholine

생성물 1

HCID 58222544(S)-4-(2-chloro-9-methyl-9H-purin-6-yl)-3-methylmorpholine수율 85.3%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 2,6-dichloro-9-methyl-9H-purine (1.41 g, 6.96 mmol) and (S)-3-methylmorpholine (817 mg, 8.08 mmol, 1.16 eq.) in anhydrous ethanol (60 mL) and anhydrous DMF (5.0 mL) was added N,N-diisopropylethylamine (1.8 mL, 10.43 mmol, 1.5 eq.), and the reaction mixture was stirred at RT under N2 for 3 days. The reaction mixture was diluted with 1:1 v/v diethyl ether:ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine, then dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 80% ethyl acetate in hexane) to give the desired compound (a-4) as a solid (1.59 g, 85.2%). 1H NMR (CDCl3, 500 MHz) δ ppm 7.65 (s, 1H), 5.34 (broad d, 2H), 3.99 (m, 1), 3.76 (m, 5H), 3.61 (ddd, 1H), 3.36 (broad s), 1H), 1.39 (d, 3H).

후처리

  1. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 80% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-e8913a2f6d604bbb84b28d207cf65046
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288381B2

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