Water → HCID 25186553, compound

HRID 750507Notes

Reaction equation

HRID 750507 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](OS(C2C=CC(C)=CC=2)(=O)=O)[C:5]([N+:19]([O-:21])=[O:20])=[C:4]([C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)[N:3]=1.C(N(CC)CC)C.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][NH2:41].O>C(COC)OC>[O:23]1[CH:24]=[CH:25][CH:26]=[C:22]1[C:4]1[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([NH:41][CH2:40][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=2)[C:5]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 25187393HCID 25187393, compound

Product 1

HCID 25186553HCID 25186553, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (2-amino-6-(2-furyl)-5-nitropyrimidin-4-yl)4-methylbenzenesulphonate (478 mg, 1.27 mmol) in dimethoxyethane (15 mL) was treated with triethylamine (0.531 mL, 3.81 mmol) and 2-pyridinemethylamine (0.393 mL, 3.81 mmol), stirred for 16 h, poured into water (100 mL) and the resulting solid was filtered to give the title compound (275 mg, 69%) as a yellow solid; NMR δH (400 MHz, CDCl3) 8.70-8.58 (2H, m), 7.70-7.66 (1H, m), 7.55-7.54 (1H, m), 7.28 (1H, d, J 8.0 Hz), 7.24-7.20 (1H, m), 7.07-7.06 (1H, m), 6.54-6.52 (1H, m), 5.26 (2H, br s) and 4.83 (2H, d, J 5.0 Hz); Retention time 1.44 min.

Workup

  1. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-a0366b826a2c49b6b848710d0fe58a43
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

Loading…