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 624607ノート

反応式

HRID 624607 の反応式
[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]

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 31272Butyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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;

後処理

  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.

出典と根拠

ORDレコード
ord-934173f491ea435981e1a44ab66fb180
出典データセット
uspto-grants-2016_04
特許番号
US09303035B2

反応ノート

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