4-Bromopyrimidine-2-carbonitrile → Ethyl 4-(3-(2-cyanopyrimidin-4-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882127ノート

反応式

HRID 882127 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:15]3[C:16]4[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][N:21]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[CH:13][CH:14]=2)O1.Br[C:39]1[CH:44]=[CH:43][N:42]=[C:41]([C:45]#[N:46])[N:40]=1>C(=O)([O-])[O-].[Na+].[Na+].COCCOC.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>[C:45]([C:41]1[N:42]=[C:43]([C:9]2[CH:10]=[C:11]([C:15]3[C:16]4[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][N:21]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[CH:13][CH:14]=2)[CH:44]=[CH:39][N:40]=1)#[N:46]

参加物

6

反応物 2

HCID 534079104-Bromopyrimidine-2-carbonitrileHCID 89629877HCID 89629877、化合物

生成物 1

HCID 89630128Ethyl 4-(3-(2-cyanopyrimidin-4-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 10340Sodium Carbonate溶媒

反応条件

温度
95 °C

実験手順

A mixture of ethyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (54.4 mg, 0.104 mmol), 4-bromopyrimidine-2-carbonitrile (38.2 mg, 0.208 mmol), and tetrakis(triphenylphosphine)palladium(0) (24 mg, 0.021 mmol) in 2 M aqueous sodium carbonate (150 uL) and DME (500 μL) was purged with argon. The reaction vessel was then sealed and heated at 95° C. overnight. The reaction mixture was filtered through Celite and rinsed with ethyl acetate. The reaction solution was concentrated under reduced pressure and the residue purified by chromatography on silica eluting with 40-60% ethyl acetatehexane to give the desired product. LRMS calc'd for C26H29N6O3Si [M+H]+: 501, found 501.

後処理

  1. customwas purged with argon
  2. customThe reaction vessel was then sealed
  3. filtrationThe reaction mixture was filtered through Celite
  4. washrinsed with ethyl acetate
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. customthe residue purified by chromatography on silica eluting with 40-60% ethyl acetatehexane

出典と根拠

ORDレコード
ord-52b0886f08984b8583dca5ffd52fcb58
出典データセット
uspto-grants-2015_03
特許番号
US08993756B2

反応ノート

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