Ammonium Hydroxide → 4-(4-(6-Methoxypyridin-3-ylamino)pyrimidin-5-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621514Notes

Reaction equation

HRID 1621514 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16]3[N:21]=[C:20]([CH3:22])[N:19]=[C:18](SC)[N:17]=3)=[CH:14][N:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.[OH-].[NH4+:26]>O1CCOCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16]3[N:21]=[C:20]([CH3:22])[N:19]=[C:18]([NH2:26])[N:17]=3)=[CH:14][N:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 60155791N-(6-methoxypyridin-3-yl)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyrimidin-4-amine

Product 1

HCID 595482834-(4-(6-Methoxypyridin-3-ylamino)pyrimidin-5-yl)-6-methyl-1,3,5-triazin-2-amineYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A glass microwave reaction vessel was charged with N-(6-methoxypyridin-3-yl)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyrimidin-4-amine (14 mg, 0.041 mmol), ammonium hydroxide, 28.0-30.0% (0.5 mL, 12.84 mmol) and dioxane (1 mL). The reaction mixture was stirred and heated at reflux in an oil bath for 1 h. The solid formed was filtered off and washed with EtOAc to give 4-(4-(6-methoxypyridin-3-ylamino)pyrimidin-5-yl)-6-methyl-1,3,5-triazin-2-amine (10 mg, 0.032 mmol, 79% yield). 1H NMR (300 MHz, d6-DMSO) δ 11.78 (s, 1H); 9.37 (s, 1H); 8.65 (s, 1H); 8.48 (s, 1H); 8.10 (d, J=8.33 Hz, 1H); 7.94 (s, 1H); 7.79 (s, 1H); 6.88 (d, J=8.77 Hz, 1H); 3.87 (s, 3H); 2.43 (s, 3H). m/z (ESI, +ve ion) 311.1 (M+H)+.

Workup

  1. customA glass microwave reaction vessel
  2. temperatureheated
  3. temperatureat reflux in an oil bath for 1 h
  4. customThe solid formed
  5. filtrationwas filtered off
  6. washwashed with EtOAc

Sources & evidence

ORD record
ord-2ae5bb0fe42843a98ecc3e115b11a7c4
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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