Diisopropylethylamine → 5-bromo-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine

HRID 1811925ノート

反応式

HRID 1811925 の反応式
[Br:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[N:6][CH:7]=1.[CH3:9][O:10][C:11]1[N:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(N(CC)C(C)C)(C)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[C:3]([NH:8][C:14]2[CH:15]=[N:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[N:4][CH:5]=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 102615764-Amino-5-bromopyrimidine

生成物 1

HCID 601557905-bromo-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine収率 6.5%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 5-bromopyrimidin-4-amine (344 mg, 1.977 mmol), 6-methoxypyridin-3-ylboronic acid (907 mg, 5.93 mmol), N,N-diisopropylethylamine (1.376 mL, 7.91 mmol) and anhydrous copper (II) acetate (539 mg, 2.97 mmol) in dichloromethane (2 mL) was stirred at room temperature overnight. The solid was filtered off and washed with CH2Cl2. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 50% EtOAc/hexanes to give 5-bromo-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine (36 mg, 0.128 mmol, 6.48% yield). 1H NMR (300 MHz, CDCl3) δ 8.55 (s, 1H); 8.46 (s, 1H); 8.28 (s, 1H); 7.85 (dd, J=8.77, 2.48 Hz, 1H); 6.98 (s, 1H); 6.80 (d, J=8.92 Hz, 1H); 3.95 (s, 3H). m/z (ESI, +ve ion) 281.0 (M+H)+.

後処理

  1. filtrationThe solid was filtered off
  2. washwashed with CH2Cl2
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with 50% EtOAc/hexanes

出典と根拠

ORDレコード
ord-6363d3f611144fd18618e357246f1899
出典データセット
uspto-grants-2013_01
特許番号
US08362241B2

反応ノート

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