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

HRID 1811925노트

반응식

HRID 1811925 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-6363d3f611144fd18618e357246f1899
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

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