Ammonia → 4-(2-((6-Methoxypyridin-3-yl)amino)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1811813Notes

Reaction equation

HRID 1811813 reaction equation
[NH3:1].CC(O)C.[CH3:6][O:7][C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]2[C:20]([C:21]3[N:26]=[C:25]([CH3:27])[N:24]=[C:23](SC)[N:22]=3)=[CH:19][C:18]([CH2:30][N:31]3[CH2:36][CH2:35][N:34]([S:37]([CH3:40])(=[O:39])=[O:38])[CH2:33][CH2:32]3)=[CH:17][N:16]=2)=[CH:10][CH:9]=1>>[CH3:6][O:7][C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]2[C:20]([C:21]3[N:26]=[C:25]([CH3:27])[N:24]=[C:23]([NH2:1])[N:22]=3)=[CH:19][C:18]([CH2:30][N:31]3[CH2:32][CH2:33][N:34]([S:37]([CH3:40])(=[O:38])=[O:39])[CH2:35][CH2:36]3)=[CH:17][N:16]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 3776IsopropanolHCID 66599816N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-amine

Product 1

HCID 497848944-(2-((6-Methoxypyridin-3-yl)amino)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amineYield 56.3%

Conditions

Temperature
90 °C

Procedure

2 M NH3 in 2-propanol (2.00 mL, 92 mmol) was added to N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-amine (221 mg, 0.428 mmol) and the mixture was sealed and heated at 90° C. overnight. After cooling, the reaction mixture was concentrated, adsorbed onto a plug of silica gel and chromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr., pre-packed silica gel column (DCM to 10% MeOH in DCM) followed by washing of the isolated solid with MeOH to give 4-(2-(6-methoxypyridin-3-ylamino)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (117 mg, 0.241 mmol, 56.3% yield) as a yellow solid. LCMS (API-ES) m/z 486 (M+H)+; 1H NMR (400 MHz, d6-DMSO) δ 11.76 (br. s., 1H) 8.71 (br. s., 1H) 8.55 (br. s., 1H) 8.03-8.28 (m, 2H) 7.87 (br. s., 1H) 7.73 (br. s., 1H) 6.82 (d, J=7.63 Hz, 1H) 3.84 (br. s., 3H) 3.48 (br. s., 2H) 3.11 (br. s., 4H) 2.87 (br. s., 3H) 2.52-2.58 (m, 3H) 2.44 (br. s., 4H).

Workup

  1. customthe mixture was sealed
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated
  4. customchromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr
  5. washby washing of the isolated solid with MeOH

Sources & evidence

ORD record
ord-4fb7db300b6148dcb14c9d4dd9fb16c8
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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