Sodium Hydroxide → 4-(5-(1-Aminoethyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621931Notes

Reaction equation

HRID 1621931 reaction equation
[NH2:1][CH:2]([C:4]1[CH:5]=[C:6]([C:20]2[N:25]=[C:24]([CH3:26])[N:23]=[C:22]([N:27](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[N:21]=2)[C:7]([NH:10][C:11]2[CH:12]=[N:13][C:14]([O:18][CH3:19])=[C:15]([F:17])[CH:16]=2)=[N:8][CH:9]=1)[CH3:3].S(O)(C(F)(F)F)(=O)=O.FC(C(O)=O)(F)F.[OH-].[Na+]>>[NH2:1][CH:2]([C:4]1[CH:5]=[C:6]([C:20]2[N:25]=[C:24]([CH3:26])[N:23]=[C:22]([NH2:27])[N:21]=2)[C:7]([NH:10][C:11]2[CH:12]=[N:13][C:14]([O:18][CH3:19])=[C:15]([F:17])[CH:16]=2)=[N:8][CH:9]=1)[CH3:3]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 18539426TfOH-TFAHCID 666120754-(5-(1-aminoethyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 595483464-(5-(1-Aminoethyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amineYield 88%

Conditions

Temperature
70 °C

Procedure

To a 25 mL round-bottomed flask was added 4-(5-(1-aminoethyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (150 mg, 0.246 mmol) and 7% TfOH-TFA (5 mL).The solution was heated at 70° C. for minutes. The mixture was cooled to 0° C. and neutralized with 10N NaOH. The obtained suspension was filtered to provide 4-(5-(1-aminoethyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (80 mg, 88% yield) as a yellow solid. m/z (ESI positive ion): 371 (M+H)+. 1H NMR 400 MHz, DMSO-d6): 6 ppm 1H NMR (400 MHz, DMSO-d6) δ ppm 1.07 (d, J=6.26 Hz, 3H) 1.75 (br s, 2H) 2.23 (s, 3H) 3.81-3.86 (m, 1H) 7.60 (d, J=61.62 Hz, 2H) 8.09-8.25 (m, 3H) 8.61 (s, 1H) 11.68 (s, 1H).

Workup

  1. filtrationThe obtained suspension was filtered

Sources & evidence

ORD record
ord-82e64d2d47724dab887a88f0ee6ebf53
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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