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Potassium Carbonate → HCID 178488429、化合物

HRID 472252
ノート
印刷プレビュー

反応式

HRID 472252 の反応式
[NH2:1][C:2]1[N:3]=[C:4]([CH3:24])[C:5]2[CH:11]=[C:10](Br)[C:9](=[O:13])[N:8]([C@H:14]3[CH2:19][CH2:18][C@@H:17]([O:20][CH2:21][CH2:22][OH:23])[CH2:16][CH2:15]3)[C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][N:34]=1>[Pd](Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([CH3:24])[C:5]2[CH:11]=[C:10]([C:36]3[CH:35]=[N:34][C:33]([O:32][CH3:31])=[CH:38][CH:37]=3)[C:9](=[O:13])[N:8]([C@H:14]3[CH2:19][CH2:18][C@@H:17]([O:20][CH2:21][CH2:22][OH:23])[CH2:16][CH2:15]3)[C:6]=2[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

5

反応物 3

HCID 11430Potassium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 178433332HCID 178433332、化合物

生成物 1

HCID 178488429HCID 178488429、化合物収率 93%

試薬・触媒・溶媒 1

HCID 24290Palladium Chloride触媒

反応条件

温度
100 °C

実験手順

A mixture of 2-amino-6-bromo-8-(cis-4-(2-hydroxyethoxy)cyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (50 mg, 0.13 mmol), potassium carbonate (52 mg, 0.38 mmol), and 2-methoxy-5-pyridine boronic acid (38 mg, 0.25 mmol) in 5:1 dimethylformade:water (1.3 mL) was bubbled with argon for 5 minutes. To the mixture was added bis(tripehnylphosphine) palladium (II) chloride (9 mg, 0.13 mmol) and the microwave vial was immediately sealed and the mixture was bubbled again with argon. After heating for 20 min at 100° C. in the microwave, the mixture was concentrated in vacuo. The residue was dissolved in CHCl3 (60 mL) and washed with water (10 mL) and brine (10 mL). The organic layer was dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0-5%) to afford the title compound (50 mg, 93%).

後処理

  1. customwater (1.3 mL) was bubbled with argon for 5 minutes
  2. customthe microwave vial was immediately sealed
  3. customthe mixture was bubbled again with argon
  4. concentrationthe mixture was concentrated in vacuo
  5. dissolutionThe residue was dissolved in CHCl3 (60 mL)
  6. washwashed with water (10 mL) and brine (10 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography
  11. washeluting with chloroform/7 N ammonia in methanol (0-5%)

出典と根拠

ORDレコード
ord-7819280752644c7682fb180eef045426
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08633204B2

反応ノート

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