Water → 5-(3-fluorophenyl)-1,3-dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 624609ノート

反応式

HRID 624609 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:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=1.[OH-].[Ba+2].[OH-].O>C(OCCCC)(=O)C.Cl>[F:32][C:28]1[CH:27]=[C:26]([C:10]2[N:9]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=[C:7]3[C:6]=2[C:5](=[O:22])[N:4]([CH3:23])[C:3](=[O:24])[N:2]3[CH3:1])[CH:31]=[CH:30][CH:29]=1

参加物

7

反応物 4

HCID 962WaterHCID 140821-Bromo-3-fluorobenzeneHCID 6093286Barium hydroxideHCID 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 867229295-(3-fluorophenyl)-1,3-dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒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 (Intermediate Ga Step 2) (7.31 g, 20.7 mmol), 1-bromo-3-fluorobenzene (2.10 mL, 18.8 mmol), Pd-118 (245 mg, 0.38 mmol), and barium hydroxide (6.44 g, 37.6 mmol) in n-butyl acetate (64 mL) was heated to 80° C. Water (4.06 mL, 226.0 mmol) was added and the mixture was stirred vigorously at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature diluted with 1M HCl(aq) (100 mL) and was extracted with DCM (3×100 mL). The combined organic layers were washed with saturated brine (1×100 mL), dried over magnesium sulfate and the evaporated under vacuum. The residue was recrystallised from methanol to afford the title compound.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionwas extracted with DCM (3×100 mL)
  3. washThe combined organic layers were washed with saturated brine (1×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. customthe evaporated under vacuum
  6. customThe residue was recrystallised from methanol

出典と根拠

ORDレコード
ord-ff2d264326dc49d19d5674e1b8ae8e55
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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