Water → HCID 25186553, compound

HRID 732981Notes

Reaction equation

HRID 732981 reaction equation
CC1C=CC(S(O[C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)[N:15]=[C:14]([NH2:26])[N:13]=2)(=O)=O)=CC=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:22]1[CH:23]=[CH:24][CH:25]=[C:21]1[C:16]1[N:15]=[C:14]([NH2:26])[N:13]=[C:12]([NH:41][CH2:40][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=2)[C:17]=1[N+:18]([O-:20])=[O:19]

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-2fbb231848f44e38964bdcdb3b7c67b5
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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