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Sodium Carbonate → 4-chloro-5-(2-methoxyphenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 882187
ノート
印刷プレビュー

反応式

HRID 882187 の反応式
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:3]2[C:10]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][CH3:20])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:4]=2[N:5]=[CH:6][N:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 27339582-Methoxyphenylboronic acidHCID 867069334-chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 896300714-chloro-5-(2-methoxyphenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 80711,2-Dimethoxyethane溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

To a nitrogen gas purged mixture of 4-chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (200 mg, 0.488 mmol), and (2-methoxyphenyl)boronic acid (96 mg, 0.64 mmol) in 2 M aqueous sodium carbonate (0.610 mL, 1.22 mmol) and DME (3.0 mL) was added tetrakis(triphenylphosphine)palladium(0) (56 mg, 0.049 mmol). The reaction was sealed and heated at 130° C. for 30 minutes. The reaction was then diluted with EtOAc and passed through a column of Celite and sodium sulfate to remove water and solids. The reaction solution was concentrated under reduced pressure and the crude product purified by silica chromatography eluting with 1-20% ethyl acetatehexane to afford 4-chloro-5-(2-methoxyphenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine as a solid. LRMS (ESI) calcd for C19H25ClN3O2Si [M+H]+: 390, found 390.

後処理

  1. customTo a nitrogen gas purged
  2. customThe reaction was sealed
  3. customto remove water and solids
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. customthe crude product purified by silica chromatography
  6. washeluting with 1-20% ethyl acetatehexane

出典と根拠

ORDレコード
ord-daa09468a94043e0b5fbf59d22e1a252
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08993756B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート