O-Methyltyramine → HCID 18982108, compound

HRID 1463269Notes

Reaction equation

HRID 1463269 reaction equation
[NH2:1][C:2]1[C:7]([N:8]=[O:9])=[C:6]([NH2:10])[N:5]=[C:4](SC)[N:3]=1.[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][CH2:20][NH2:21])=[CH:17][CH:16]=1>O>[NH2:1][C:2]1[C:7]([N:8]=[O:9])=[C:6]([NH2:10])[N:5]=[C:4]([NH:21][CH2:20][CH2:19][C:18]2[CH:22]=[CH:23][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[N:3]=1

Participants

4

Reactant 2

HCID 4657O-MethyltyramineHCID 3276844,6-Pyrimidinediamine, 2-(methylthio)-5-nitroso-

Product 1

HCID 18982108HCID 18982108, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4,6-diamino-2-methylthio-5-nitrosopyrimidine (10 g, 5.4 mM), 4-methoxyphenethylamine (7.92 ml, 5.4 mM) and water (180 ml) was heated to reflux for one hour. After cooling the red solid was separated by filtration, washed with water, and dried. There was thus obtained 4,6-diamino-2-[2-(4-methoxyphenyl)ethyl]amino-5-nitrosopyrimidine (13.4 g, 84% yield). NMR: DMSO-d6 ; 2.7-2.85(m,2H, CH2 --CH2), 3.4-3.6(m, 2H, CH2 --NH), 3.7 (s, 3H, OCH3), 6.75-6.8(m,2H, aromatic-H), 7.05-7.25 (m, 2H, aromatic-H), 7.4-10.5 (m, 5H, NH2 ×2, NH), m/e [M+H[+ 289.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for one hour
  3. temperatureAfter cooling the red solid
  4. customwas separated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ef8c6785a21945508157d766f6bbd8a3
Source dataset
uspto-grants-1994_04
Patent number
US05300509

Reaction notes

Loading…