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

HRID 882188
ノート
印刷プレビュー

反応式

HRID 882188 の反応式
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:4]=2[N:5]=[CH:6][N:7]=1.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:3]2[C:2]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:7][CH:6]=[N:5][C:4]=2[N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:9]=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

7

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 896300714-chloro-5-(2-methoxyphenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 896301495-(2-methoxyphenyl)-4-phenyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

試薬・触媒・溶媒 3

HCID 178418807
HCID 178418807、化合物
触媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To a nitrogen gas purged mixture of 4-chloro-5-(2-methoxyphenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (50 mg, 0.13 mmol) and phenyl boronic acid (23.5 mg, 0.192 mmol) in 2 M potassium carbonate (0.192 mL, 0.385 mmol) and tetrahydrofuran (1.0 mL) was added PdCl2(dppf)-CH2Cl2 (10 mg, 0.013 mmol). The reaction was sealed and heated to 120° C. for 20 minutes. Upon cooling, the reaction mixture was diluted with EtOAc and washed with saturated sodium bicarbonate and brine. The organic layer was then dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica chromatography eluting with 1-20% ethyl acetate/hexanes to afford 5-(2-methoxyphenyl)-4-phenyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. LRMS (ESI) calcd for C25H30N3O2Si [M+H]+: 432, found 432.

後処理

  1. customTo a nitrogen gas purged
  2. customThe reaction was sealed
  3. temperatureUpon cooling
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialThe organic layer was then dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica chromatography
  9. washeluting with 1-20% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-4e21611589ec4001b3cb9d30cbec60aa
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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