Tetrahydrofuran → 12-Bromo-6-chloro-15-oxa-2,4,8,25-tetraazatetracyclo[17.3.1.1(3,7).1(10,14)]pentacosa-1(23),3(25),4,6,10(24),11,13,19,21-nonaene

HRID 1614977Notes

Reaction equation

HRID 1614977 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:28])[CH:5]=[C:6]([CH2:8][NH:9][C:10]2[C:15]([Cl:16])=[CH:14][N:13]=[C:12]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][CH2:26]Br)[CH:19]=3)[N:11]=2)[CH:7]=1.O1CCCC1.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]2[CH:5]=[C:6]([CH2:8][NH:9][C:10]3[N:11]=[C:12]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([CH:19]=4)[CH2:24][CH2:25][CH2:26][O:28]2)[N:13]=[CH:14][C:15]=3[Cl:16])[CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 584679133-Bromo-5-{[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol

Product 1

HCID 4686474912-Bromo-6-chloro-15-oxa-2,4,8,25-tetraazatetracyclo[17.3.1.1(3,7).1(10,14)]pentacosa-1(23),3(25),4,6,10(24),11,13,19,21-nonaeneYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a reaction flask were added 3-bromo-5-{[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol (2.97 g, 5.64 mmol), tetrahydrofuran (30 mL), and a solution of sodium hydroxide in water (33.8 mL, 1.0 M). The reaction mixture was stirred at rt over two days. The mixture was filtered, and then the cake was washed with water, MeOH, and EtOAc successively to provide the desired product (1.33 g, 53%) as an off-white powder. LCMS for C20H18BrClN4O (M+H)+: m/z=444.9, 446.9. 1H NMR (400 MHz, DMSO-d6): δ 9.04 (s, 1H), 7.95 (s, 1H), 7.93 (s, 1H), 7.36 (s, 1H), 7.10 (m, 1H), 7.07 (m, 1H), 6.92 (d, J=7.9 Hz, 1H), 6.86 (s, 1H), 6.78 (d, J=7.5 Hz, 1H), 4.42 (d, J=5.5 Hz, 2H), 4.18 (t, 2H), 3.60 (m, 1H), 2.65 (m, 2H), 1.65 (m, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe cake was washed with water, MeOH, and EtOAc successively

Sources & evidence

ORD record
ord-b5ace2a8188f431bae375ea1d35edf74
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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