Ammonia → HCID 59548403, compound

HRID 1811916Notes

Reaction equation

HRID 1811916 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)=[N:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.[NH3:25]>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]([NH2:25])[N:17]=3)=[N:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66611421HCID 66611421, compound

Product 1

HCID 59548403HCID 59548403, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A glass microwave reaction vessel was charged with N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyrazin-2-amine (44 mg, 0.129 mmol) and ammonia (1 mL, 37% in water) in dioxane (1 mL). The reaction mixture was stirred and heated at 100° C. for 16 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 10% MeOH/EtOAc to give 4-(3-(6-methoxypyridin-3-ylamino)pyrazin-2-yl)-6-methyl-1,3,5-triazin-2-amine (34 mg, 0.110 mmol, 85% yield) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 11.83 (s, 1H); 8.37 (d, J=2.05 Hz, 1H); 8.24 (s, 1H); 8.20 (s, 1H); 8.04 (dd, J=8.92, 2.48 Hz, 1H); 6.80 (d, J=8.77 Hz, 1H); 5.71 (s, 2H); 3.95 (s, 3H); 2.62 (s, 3H). m/z (ESI, +ve ion) 311.0 (M+H)+.

Workup

  1. customA glass microwave reaction vessel
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with 10% MeOH/EtOAc

Sources & evidence

ORD record
ord-c3fe3529273940b9a95a87c9fa4a0a7f
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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