Sodium hydride → 1-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyrimidin-4-yl)propan-2-ol

HRID 1773278노트

반응식

HRID 1773278 반응식
[H-].[Na+].[CH3:3][N:4]1[CH2:17][CH2:16][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1.[CH3:18][C:19]1([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][N:23]=2)[CH2:21][O:20]1>CCCCCC.CN(C=O)C>[CH3:3][N:4]1[CH2:17][CH2:16][C:7]2[N:8]([CH2:18][C:19]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][N:23]=3)([OH:20])[CH3:21])[C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 594549674-(2-Methyloxiran-2-yl)pyrimidine

생성물 1

HCID 497794431-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyrimidin-4-yl)propan-2-ol수율 52%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8058Hexane용매

실험 절차

Sodium hydride (200 mg, 8.33 mmol) was washed with hexane and dried under vacuum. DMF (4 mL) was added, resulting in a suspension. 2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (400 mg, 2 mmol) in 2 mL DMF was added dropwise and stirred for 30 min at RT. 4-(2-Methyl-oxiranyl)-pyrimidine (490 mg, 3.60 mmol) in 2 mL DMF was added dropwise and the reaction mixture was stirred overnight at RT. After the completion of reaction, the reaction mixture was quenched with ice-cold water and extracted three times with EtOAc. The combined organic layers were washed with water several times followed by brine, and then dried over sodium sulfate. The solvent was evaporated and the residue washed with hexane and crystallized from ether-DCM and hexane to obtain 350 mg of desired product. 1HNMR (CD3OD, Oxalate salt) d (ppm): 9.10 (s, 1H), 8.50 (d, 1H), 7.50 (d, 1H), 7.10 (s, 1H), 6.95 (d, 1H), 6.80 (d, 1H), 4.40 (m, 4H), 3.60 (m, 2H), 3.40 (m, 1H), 3.20 (m, 1H), 3.0 (s, 3H), 2.50 (s, 3H), 1.60 (s, 3H).

후처리

  1. customdried under vacuum
  2. additionDMF (4 mL) was added
  3. customresulting in a suspension
  4. stirringthe reaction mixture was stirred overnight at RT
  5. customAfter the completion of reaction
  6. customthe reaction mixture was quenched with ice-cold water
  7. extractionextracted three times with EtOAc
  8. washThe combined organic layers were washed with water several times
  9. dry with materialdried over sodium sulfate
  10. customThe solvent was evaporated
  11. washthe residue washed with hexane
  12. customcrystallized from ether-DCM and hexane

출처 및 근거

ORD 기록
ord-93fe2fd6bbf24a9ab355388203dd2da3
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255094B2

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