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 624607노트

반응식

HRID 624607 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. The resulting residue was re-crystallised from methanol and dried under vacuum at 50° C. to afford the title compound;

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
  7. customThe resulting residue was re-crystallised from methanol
  8. customdried under vacuum at 50° C.

출처 및 근거

ORD 기록
ord-934173f491ea435981e1a44ab66fb180
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303035B2

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