2-Morpholinoethylamine → 4-Chloro-N-(2-morpholinoethyl)thieno[3,2-d]pyrimidine-6-carboxamide

HRID 1261193노트

반응식

HRID 1261193 반응식
[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:11](Cl)=[O:12])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:11]([NH:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:12])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

4

반응물 2

HCID 4082852-MorpholinoethylamineHCID 594245464-Chlorothieno[3,2-d]pyrimidine-6-carbonyl chloride

생성물 1

HCID 594244794-Chloro-N-(2-morpholinoethyl)thieno[3,2-d]pyrimidine-6-carboxamide수율 65.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 22 (500 mg, 2.15 mmol) in anhydrous DCM (20 mL) at 0° C. under nitrogen was added 4-(2-aminoethyl)-morpholine (307 mg, 2.36 mmol). The reaction mixture was allowed to warm to the room temperature over 3 hours and was stirred for additional 14 hours, treated with saturated aqueous solution of NHCO3 and extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated. The residues was purified by flash chromatography on silica gel (eluents MeOH-DCM, 5:95, then 1:9) to afford the title compound 23 (458 mg, 65% yield) as a white solid 1H NMR (400 MHz, CDCl3) δ(ppm): 9.13 (t, J=5.6 Hz, 1H), 9.08 (s, 1H), 8.32 (s, 1H), 3.60-3.54 (m, 4H), 3.44 (q, J=6.8 Hz, 2H), 2.54-2.48 (m, 2H), 2.46-2.40 (m, 4H).

후처리

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residues was purified by flash chromatography on silica gel (eluents MeOH-DCM, 5:95

출처 및 근거

ORD 기록
ord-124df1ff08a341b9baa441cae006f068
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470850B2

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