Sodium Iodide → 2-(4-(5-Bromopyrimidin-2-ylamino)phenyl)ethanol

HRID 2067869Notes

Reaction equation

HRID 2067869 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[Br:11][C:12]1[CH:13]=[N:14][C:15](Cl)=[N:16][CH:17]=1.[I-].[Na+].C(N(C(C)C)CC)(C)C>C(O)CCC.O>[Br:11][C:12]1[CH:13]=[N:14][C:15]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=2)=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 669044-Aminophenethyl alcoholHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 576326232-(4-(5-Bromopyrimidin-2-ylamino)phenyl)ethanol

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-(4-aminophenyl)ethanol (0.72 mol), 5-bromo-2-chloropyrimidine 4 (0.72 mol), sodium iodide (0.72 mol), and diisopropylethylamine (1.45 mol) in n-butanol (400 mL) is heated at reflux for 16 h. The reaction is cooled to rt and the mixture is diluted with water. The light yellow solid that precipitates is filtered to give 2-(4-(5-bromopyrimidin-2-ylamino)phenyl)ethanol 18. 1H NMR (300 MHz, d6-DMSO) δ 9.72 (s, 1H), 8.52 (s, 2H), 7.55 (m, 2H), 7.09 (d, 2H), 4.64 (m, 1H), 3.52 (m, 2H), 2.65 (m, 2H). MS (m/z) (M+1)+: 294.1, 296.1.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 h
  3. customThe light yellow solid that precipitates
  4. filtrationis filtered

Sources & evidence

ORD record
ord-849254bef3c348d29e4211f969ce1878
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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