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 2201182Notes

Reaction equation

HRID 2201182 reaction equation
[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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 31272Butyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a9df3f0ad582402c86ffea2ec1a57320
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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