Hydrochloric Acid → HCID 178492153, compound

HRID 1621431Notes

Reaction equation

HRID 1621431 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16]3[N:24]=[C:23]([CH3:25])[N:22]=[C:21]4[C:17]=3[N:18]=[CH:19][N:20]4C3CCCCO3)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.Cl>>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16]3[N:24]=[C:23]([CH3:25])[N:22]=[C:21]4[C:17]=3[N:18]=[CH:19][NH:20]4)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 601548206-methoxy-N-(3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)pyridin-3-amine

Product 1

HCID 178492153HCID 178492153, compoundYield 95%

Procedure

A solution of 6-methoxy-N-(3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)pyridin-3-amine (95.3 mg, 228 μmol) in 2N aqueous HCl (2.0 mL, 4 mmol) was heated briefly at 100° C. in an oil bath, and then the heater was turned off and the mixture allowed to slowly cool. The solution was concentrated and purified by SCX ion exchange chromatography washing with MeOH and eluting off with 2N NH3/MeOH to give N-(6-methoxypyridin-3-yl)-3-(2-methyl-9H-purin-6-yl)pyridin-2-amine (72 mg, 95% yield) as an orange solid. 1H NMR (400 MHz, d6-DMSO) δ 13.60 (br. s., 1H); 12.68 (s, 1H); 9.80 (dd, J=7.82, 1.96 Hz, 1H); 8.60 (s, 1H); 8.54 (d, J=2.69 Hz, 1H); 8.31 (dd, J=4.65, 1.96 Hz, 1H); 8.20 (dd, J=8.92, 2.81 Hz, 1H); 7.00 (dd, J=7.95, 4.77 Hz, 1H); 6.85 (d, J=8.80 Hz, 1H); 3.85 (s, 3H); 2.86 (s, 3H). m/z (ESI, +ve) 334.0 (M+H)+.

Workup

  1. temperatureto slowly cool
  2. concentrationThe solution was concentrated
  3. custompurified by SCX ion exchange chromatography
  4. washwashing with MeOH
  5. washeluting off with 2N NH3/MeOH

Sources & evidence

ORD record
ord-2db39db6e67e4dbf82d266f3d1080fee
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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