Hydrochloric Acid → 6-(6-Methoxypyridin-3-ylamino)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)nicotinaldehyde

HRID 1811824Notes

Reaction equation

HRID 1811824 reaction equation
Cl.[O:2]1CCO[CH:3]1[C:7]1[CH:8]=[C:9]([C:22]2[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([S:29][CH3:30])[N:23]=2)[C:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[N:11][CH:12]=1.C1COCC1>>[CH3:21][O:20][C:17]1[N:16]=[CH:15][C:14]([NH:13][C:10]2[C:9]([C:22]3[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([S:29][CH3:30])[N:23]=3)=[CH:8][C:7]([CH:3]=[O:2])=[CH:12][N:11]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 666112635-(1,3-dioxolan-2-yl)-N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyridin-2-amine

Product 1

HCID 866470496-(6-Methoxypyridin-3-ylamino)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)nicotinaldehydeYield 86%

Conditions

Temperature
25 °C

Procedure

2 M Aqueous HCl (1.50 mL, 3.00 mmol) was added to a stirred solution of 5-(1,3-dioxolan-2-yl)-N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyridin-2-amine (35 mg, 0.085 mmol) in THF (3.00 mL, 36.6 mmol) and the mixture was stirred at 25° C. for 2 h. A yellow precipitate gradually formed. The volatile solvents were minimized and the precipitate was collected and dried to give 6-(6-methoxypyridin-3-ylamino)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)nicotinaldehyde (27 mg, 0.073 mmol, 86% yield) as a yellow solid. LCMS (API-ES) m/z 369 (M+H)+.

Workup

  1. customA yellow precipitate gradually formed
  2. customthe precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-df4faf0ffbe44391bdd0be257db116e9
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

Loading…