Methylamine → HCID 59394609, compound

HRID 453202Notes

Reaction equation

HRID 453202 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[N:17]=[CH:16][N:15]=[C:14]([CH2:18]OS(C)(=O)=O)[CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:24])[NH:6]2.[CH3:25][NH2:26].C1COCC1>C(Cl)Cl.O.CCOC(C)=O>[F:1][C:2]1[C:10]([O:11][C:12]2[N:17]=[CH:16][N:15]=[C:14]([CH2:18][NH:26][CH3:25])[CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:24])[NH:6]2

Participants

7

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 59394089Methanesulfonic acid 6-(4-fluoro-2-methyl-1H-indol-5-yloxy)-pyrimidin-4-ylmethyl ester

Product 1

HCID 59394609HCID 59394609, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonic acid 6-(4-fluoro-2-methyl-1H-indol-5-yloxy)-pyrimidin-4-ylmethyl ester (2.5 g, 8.78 mmol) is stirred in DCM (40.0 mL) with 1 M methylamine in THF (4.39 mL, 8.78 mmol) at rt for 24 h. The reaction is diluted with H2O and EtOAc. The organic layer is washed with brine, dried over Na2SO4, filtered, and purified by FCC eluting with first 10-100% EtOAc in heptanes, then washing with 0-25% MeOH with NH3 in EtOAc to provide the title compound. MS (ESI) m/z 287.2 (M+1); 1H NMR (400 MHz, MeOD) δ ppm 8.63 (d, J=1.01 Hz, 1 H) 7.11 (d, J=8.59 Hz, 1 H) 7.02 (s, 1 H) 6.85 (dd, J=8.59, 7.33 Hz, 1 H) 6.23 (s, 1 H) 3.81 (s, 2 H) 2.41 (s, 3 H) 2.44 (s, 3 H).

Workup

  1. washThe organic layer is washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. custompurified by FCC
  5. washeluting with first 10-100% EtOAc in heptanes
  6. washwashing with 0-25% MeOH with NH3 in EtOAc

Sources & evidence

ORD record
ord-b1b2386dd9ff4871b672d2a1890ae762
Source dataset
uspto-grants-2013_07
Patent number
US08492393B2

Reaction notes

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