Sodium hydride → (8S)-2-chloro-9-(2-oxo-2-pyrid-3-ylethyl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

HRID 633705

반응식

HRID 633705 반응식
[H-].[Na+].[Cl:3][C:4]1[N:5]=[C:6]2[NH:14][C@H:13]([C:15]([F:18])([F:17])[F:16])[CH2:12][CH2:11][N:7]2[C:8](=[O:10])[CH:9]=1.Br.Br[CH2:21][C:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23]>CN(C=O)C>[Cl:3][C:4]1[N:5]=[C:6]2[N:14]([CH2:21][C:22](=[O:23])[C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[C@H:13]([C:15]([F:16])([F:17])[F:18])[CH2:12][CH2:11][N:7]2[C:8](=[O:10])[CH:9]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27762343-(2-Bromoacetyl)pyridine hydrobromideHCID 136238740(S)-8-chloro-2-(trifluoromethyl)-3,4-dihydro-1H-pyrimido[1,2-a]pyrimidin-6(2H)-one

생성물 1

HCID 118194423(8S)-2-chloro-9-(2-oxo-2-pyrid-3-ylethyl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

A suspension of 750 mg (15.77 mmol) of sodium hydride in 50 mL of DMF is cooled to 0° C. under argon. A solution of 2 g (7.89 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one in 50 mL of DMF is added dropwise. The mixture is stirred for 10 minutes at room temperature. After cooling the reaction medium to 0° C., 2.92 g (9.86 mmol) of 3-(bromoacetyl)pyridine hydrobromide are added portionwise. The reaction mixture is allowed to warm to room temperature and is stirred overnight. The reaction medium is evaporated to dryness and the residue is taken up in water and extracted with EtOAc. The organic phase is dried over magnesium sulfate and evaporated to dryness. The crude product obtained is purified by chromatography on silica gel (eluent: 100% EtOAc). After evaporating the fractions under reduced pressure, 1.90 g of (8S)-2-chloro-9-(2-oxo-2-pyrid-3-ylethyl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one are obtained, the characteristics of which are as follows:

후처리

  1. temperatureAfter cooling the reaction medium to 0° C.
  2. temperatureto warm to room temperature
  3. stirringis stirred overnight
  4. customThe reaction medium is evaporated to dryness
  5. extractionextracted with EtOAc
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-9c4f5da698fd4eec8ca23b1dcc091fd4
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321790B2

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