Trifluoroacetic acid → N5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-5-methoxypyridin-2-YL)-2-chloropyridine-3,5-diamine

HRID 1812422Notes

Reaction equation

HRID 1812422 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[C:10]([NH:17][C:18]3[CH:19]=[C:20]([NH:25]C(=O)OC(C)(C)C)[C:21]([Cl:24])=[N:22][CH:23]=3)=[N:11][CH:12]=[C:13]([O:15][CH3:16])[CH:14]=2)[N:3]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[C:10]([NH:17][C:18]3[CH:19]=[C:20]([NH2:25])[C:21]([Cl:24])=[N:22][CH:23]=3)=[N:11][CH:12]=[C:13]([O:15][CH3:16])[CH:14]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86647088Tert-butyl 5-(3-(4-amino-6-methyl-1,3,5-triazin-2-YL)-5-methoxypyridin-2-ylamino)-2-chloropyridin-3-ylcarbamate

Product 1

HCID 59548238N5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-5-methoxypyridin-2-YL)-2-chloropyridine-3,5-diamineYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 mL scintillation vial which contained tert-butyl 5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methoxypyridin-2-ylamino)-2-chloropyridin-3-ylcarbamate (0.210 g, 0.458 mmol) in DCM (5 mL) was added trifluoroacetic acid (Aldrich) (0.170 mL, 2.288 mmol). The resulting mixture was capped and stirred at rt in closed system for 1 h. The reaction mixture was first neutralized with sat. NaHCO3 then extracted with CHCl3 (3×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified using the column chromatography (40 g, 3% to 5% MeOH in DCM) to afford the desired product as a yellow solid (135 mg). MS (ESI pos. ion) m/z: 359.0. Calc'd exact mass for C15H15Cl N8O: 358.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.45 (s, 3H) 3.84 (s, 3H) 5.43 (s, 2H) 7.78 (br. s., 1H) 7.86 (br. s., 1H) 7.89 (d, J=2.35 Hz, 1H) 7.94 (d, J=2.15 Hz, 1H) 8.16 (d, J=3.13 Hz, 1H) 8.40 (d, J=3.13 Hz, 1H) 11.75 (s, 1H).

Workup

  1. customThe resulting mixture was capped
  2. extractionthen extracted with CHCl3 (3×10 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-faf3b7f2ae144458b2e5b355d8ad4223
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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