N,N,N',N'-Tetramethylethylenediamine → HCID 86667350, 화합물

HRID 334132

반응식

HRID 334132 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][C:13]([CH3:16])([OH:15])[CH3:14])=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:3]=1.CN(C)CCN(C)C.C([Li])CCC.CCCCCC.ClCC[I:45]>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([I:45])[N:8]2[CH2:11][CH2:12][C:13]([CH3:16])([OH:15])[CH3:14])=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:3]=1

참가 물질

7

반응물 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 1364381-Chloro-2-iodoethaneHCID 86667351HCID 86667351, 화합물HCID 178418339Butyllithium

생성물 1

HCID 86667350HCID 86667350, 화합물수율 78.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A solution of 4-(2-chloro-6-morpholino-9H-purin-9-yl)-2-methylbutan-2-ol (360 mg, 1.1 mmol) and N,N,N′,N′-tetramethylethylenediamine (0.25 mL, 1.7 mmol) in THF (8.1 mL) was cooled to −42° C. and treated with a solution of 2.5M n-butyllithium in hexane (BuLi, 2.0 mL, 5.0 mmol) dropwise over 5 minutes. After 30 minutes at −42° C., 1-chloro-2-iodoethane (0.51 mL, 5.4 mmol) was added and the reaction mixture was slowly warmed to 0° C. over 1 hr. The mixture was quenched with a saturated solution of NH4Cl, and diluted with ethyl acetate. The aqueous layer was extracted into ethyl acetate (3×), and the combined organics were dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford 4-(2-chloro-8-iodo-6-morpholino-9H-purin-9-yl)-2-methylbutan-2-ol as a white foam (390 mg, 78%). LC/MS (ESI+): m/z 452 (M+H)

후처리

  1. customThe mixture was quenched with a saturated solution of NH4Cl
  2. additiondiluted with ethyl acetate
  3. extractionThe aqueous layer was extracted into ethyl acetate (3×)
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. customabsorbed onto celite for purification by flash chromatography

출처 및 근거

ORD 기록
ord-3abe81a3204e4a34be21a45b4d36d231
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883799B2

연결된 노트

불러오는 중…