Potassium Carbonate → 3-(1,3-Dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

HRID 2201182노트

반응식

HRID 2201182 반응식
[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:10](B(O)O)=[C:6]2[C:5](=[O:22])[N:4]([CH3:23])[C:3]1=[O:24].Br[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[C:29]#[N:30].C(=O)([O-])[O-].[K+].[K+]>C(OCCCC)(=O)C.O>[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:10]([C:26]3[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=3)[C:29]#[N:30])=[C:6]2[C:5](=[O:22])[N:4]([CH3:23])[C:3]1=[O:24]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 233813-BromobenzonitrileHCID 867229261,3-Dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-ylboronic acid

생성물 1

HCID 867229273-(1,3-Dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

시약·촉매·용매 2

HCID 962Water용매2회HCID 31272Butyl Acetate용매

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온도
80 °C

실험 절차

A mixture of 1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-ylboronic acid (step 2) (2.0 g, 5.7 mmol), 3-bromobenzonitrile (937 mg, 5.2 mmol), Pd-118 (168 mg, 0.26 mmol) and potassium carbonate (1.42 g, 10.3 mmol) in n-butyl acetate (40 mL) was heated to 80° C., then water (2.23 mL, 124.0 mmol) was added and the mixture was heated at 80° C. for 90 minutes. The reaction mixture was diluted with water (100 mL), the layers were separated as much as possible, and the aqueous phase (and residual organic portion) was extracted with DCM (1×100 mL, 2×50 mL). The combined organic extracts were washed with brine (1×100 mL), dried with magnesium sulfate and the solvent was removed under vacuum.

후처리

  1. temperaturethe mixture was heated at 80° C. for 90 minutes
  2. customthe layers were separated as much as possible, and the aqueous phase (and residual organic portion)
  3. extractionwas extracted with DCM (1×100 mL, 2×50 mL)
  4. washThe combined organic extracts were washed with brine (1×100 mL)
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-a9df3f0ad582402c86ffea2ec1a57320
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359381B2

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