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

HRID 1621512Notes

Reaction equation

HRID 1621512 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-7edf7a3c9c0e459d9bec996bfa96a875
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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