Triethylamine → 3-(2-Chloropyrimidin-4-yl)-8-oxa-3-azabicyclo[3,2,1]octane

HRID 75408

반응식

HRID 75408 반응식
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.Cl.[CH:10]12[O:17][CH:14]([CH2:15][CH2:16]1)[CH2:13][NH:12][CH2:11]2.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:7]=[C:6]([N:12]2[CH2:11][CH:10]3[O:17][CH:14]([CH2:15][CH2:16]3)[CH2:13]2)[CH:5]=[CH:4][N:3]=1.[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:12]2[CH2:11][CH:10]3[O:17][CH:14]([CH2:15][CH2:16]3)[CH2:13]2)[N:7]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochloride

생성물 2

HCID 663715273-(2-Chloropyrimidin-4-yl)-8-oxa-3-azabicyclo[3,2,1]octane수율 89%HCID 866658783-(4-Chloro-pyrimidin-2-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane수율 4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A 745 mg (5 mmol) portion 2,4-dichloropyrimidine (1) was dissolved in 20 mL EtOH at 0 C. 8-oxa-3-aza-bicyclo[3.2.1]octane hydrochloride (2, 748 mg, 5 mmol) was added followed by the addition of NEt3 (2.1 mL, 15 mmol). The mixture was stirred for 1 hour at ambient temperature. The mixture was concentrated, dissolved in EtOAc and washed with saturated NaHCO3. The aqueous phase was extracted with EtOAc and the combined organic phases were dried (MgSO4), filtered and concentrated. The mixture was purified by silica gel chromatography (20-70% EtOAc in hexanes) to give 1,003 mg (4.4 mmol, 89%) of 3-(2-chloro-pyrimidin-4-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane (3) along with 50 mg (0.22 mmol, 4%) of 3-(4-chloro-pyrimidin-2-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane (4).

후처리

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with saturated NaHCO3
  4. extractionThe aqueous phase was extracted with EtOAc
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe mixture was purified by silica gel chromatography (20-70% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-42bc12a8e8aa4652ad482317cfda17d5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835429B2

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