Ammonia → N-(3-(6-amino-2-methylpyrimidin-4-yl)pyrazin-2-yl)-1H-indazol-4-amine

HRID 1621495Notes

Reaction equation

HRID 1621495 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([NH:14][C:15]3[C:16]4[CH:17]=[N:18][NH:19][C:20]=4[CH:21]=[CH:22][CH:23]=3)=[N:10][CH:11]=[CH:12][N:13]=2)[CH:5]=[C:4](S(C)=O)[N:3]=1.[NH3:27]>>[NH2:27][C:4]1[N:3]=[C:2]([CH3:1])[N:7]=[C:6]([C:8]2[C:9]([NH:14][C:15]3[C:16]4[CH:17]=[N:18][NH:19][C:20]=4[CH:21]=[CH:22][CH:23]=3)=[N:10][CH:11]=[CH:12][N:13]=2)[CH:5]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 68516415N-(3-(2-Methyl-6-(methylsulfinyl)pyrimidin-4-YL)pyrazin-2-YL)-1H-indazol-4-amine

Product 1

HCID 49785340N-(3-(6-amino-2-methylpyrimidin-4-yl)pyrazin-2-yl)-1H-indazol-4-amineYield 39%

Conditions

Temperature
100 °C

Procedure

The mixture from Step 3 was treated with ammonia (30% in water) in a sealed tube. The mixture was stirred at 100° C. overnight. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 50% THF/CH2Cl2 to give N-(3-(6-amino-2-methylpyrimidin-4-yl)pyrazin-2-yl)-1H-indazol-4-amine (7 mg, 39% yield) as a yellow solid. 1H NMR (300 MHz, d6-DMSO) δ 13.17 (s, 1H); 12.95 (s, 1H); 8.37 (d, J=2.05 Hz, 1H); 8.25 (s, 1H); 8.18 (d, J=2.05 Hz, 1H); 8.10 (d, J=7.75 Hz, 1H); 7.45 (s, 1H); 7.33 (t, J=8.11 Hz, 1H); 7.19 (d, J=7.31 Hz, 1H); 2.65 (s, 3H). m/z (ESI, +ve ion) 319 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 50% THF/CH2Cl2

Sources & evidence

ORD record
ord-5e6524db5bea4209aace0ad07dd15eb0
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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