Triethylamine → 3-(2,6-Dichloro-pyrimidin-4-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane

HRID 75410

反応式

HRID 75410 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.Cl.[CH:11]12[O:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][NH:13][CH2:12]2.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:12][CH:11]3[O:18][CH:15]([CH2:16][CH2:17]3)[CH2:14]2)[CH:5]=[C:6]([Cl:8])[N:7]=1.[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([N:13]2[CH2:12][CH:11]3[O:18][CH:15]([CH2:16][CH2:17]3)[CH2:14]2)[N:3]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 773782,4,6-TrichloropyrimidineHCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochloride

生成物 2

HCID 866658793-(2,6-Dichloro-pyrimidin-4-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane収率 83%HCID 866658803-(4,6-Dichloro-pyrimidin-2-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane収率 11%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2,4,6-Trichloropyrimidine (8, 6.325 mL, 55 mmol) was dissolved in 220 mL EtOH at 0° C. 8-Oxa-3-aza-bicyclo[3.2.1]octane hydrochloride (2, 8.23 g, 55 mmol) was added followed by the addition of NEt3 (23.1 mL, 165 mmol). The mixture was allowed to warm to room temperature and 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 the combined organic phases were dried (MgSO4), filtered, and concentrated. The mixture was purified by silica gel chromatography (10-80% EtOAc in hexanes) to give 11.807 g (45 mmol, 83%) of 3-(2,6-dichloro-pyrimidin-4-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane (9) along with 1.631 g (6.2 mmol, 11%) of 3-(4,6-dichloro-pyrimidin-2-yl)-8-oxa-3-aza-bicyclo[3.2.1]octane (10).

後処理

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with saturated NaHCO3
  4. extractionThe aqueous phase was extracted with EtOAc the combined organic phases
  5. dry with materialwere dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe mixture was purified by silica gel chromatography (10-80% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-7ccd338c5fbb421d822032d9cc5cadba
出典データセット
uspto-grants-2014_09
特許番号
US08835429B2

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