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Triethylamine → (8S)-9-(3-methyl-2-oxobutyl)-2-(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

HRID 633704
ノート
印刷プレビュー

反応式

HRID 633704 の反応式
Cl[C:2]1[N:3]=[C:4]2[N:12]([CH2:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[C@H:11]([C:19]([F:22])([F:21])[F:20])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.Cl.[C@H:24]12[CH2:30][C@H:27]([NH:28][CH2:29]1)[CH2:26][O:25]2.C(N(CC)CC)C>C(OCC)(=O)C>[CH3:16][CH:15]([CH3:17])[C:14](=[O:18])[CH2:13][N:12]1[C:4]2=[N:3][C:2]([N:28]3[CH2:29][C@@H:24]4[CH2:30][C@H:27]3[CH2:26][O:25]4)=[CH:7][C:6](=[O:8])[N:5]2[CH2:9][CH2:10][C@H:11]1[C:19]([F:22])([F:21])[F:20]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochlorideHCID 118194457(8S)-2-chloro-9-(3-methyl-2-oxobutyl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

生成物 1

HCID 72708977(8S)-9-(3-methyl-2-oxobutyl)-2-(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one収率 49%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

220 mg (0.51 mmol) of (8S)-2-chloro-9-(3-methyl-2-oxobutyl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 105.99 mg (0.78 mmol) of (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride are mixed together. The powder obtained is placed in a tube and 227 μl (1.63 mmol) of triethylamine are added. The tube is sealed and heated at 130° C. in an oil bath for 3 hours. The crude product obtained is taken up in ethyl acetate and the organic phase is washed with water, dried over magnesium sulfate and then evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 95/5 EtOAc/MeOH) to give 100 mg of (8S)-9-(3-methyl-2-oxobutyl)-2-(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, the characteristics of which are as follows:

後処理

  1. customThe powder obtained
  2. customis placed in a tube
  3. customThe tube is sealed
  4. customThe crude product obtained
  5. washthe organic phase is washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness
  8. customThe residue is purified by chromatography on silica gel (eluent: 95/5 EtOAc/MeOH)

出典と根拠

ORDレコード
ord-d199ad387da34cb993a55dfac3b46318
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321790B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート