2-Pyrimidinamine, 4-chloro-6-methoxy- → 4-Methoxy-2-pyrimidinamine

HRID 1920820Notes

Reaction equation

HRID 1920820 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.C(N(C(C)C)CC)(C)C>CCOC(C)=O.C(O)C.[Pd]>[CH3:9][O:8][C:6]1[CH:7]=[CH:2][N:3]=[C:4]([NH2:10])[N:5]=1

Participants

6

Reactant 2

HCID 798112-Pyrimidinamine, 4-chloro-6-methoxy-HCID 81531Diisopropylethylamine

Product 1

HCID 674284-Methoxy-2-pyrimidinamineYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-6-methoxypyrimidine-2-ylamine (4.4 g, 27.7 mmol) in EtOAc (200 mL) and ethanol (150 mL), was added diisopropylethylamine (9.6 mL, 55.3 mmol) and 10% palladium on carbon (2.9 g, 2.77 mmol). The heterogeneous solution was stirred under a balloon atmosphere of H2 for 14 hours, at which time the solution was filtered through a Celite pad and the volatiles were removed in vacuo. The residue was dissolved in EtOAc (200 mL), washed with Na2CO3(sat) (100 mL) and with NaCl(sat.) (100 mL), dried over Na2SO4, filtered and concentrated yielding 3.1 g (90%) of 4-methoxypyrimidine-2-ylamine. LCMS (m/z): 126 (MH+). 1H NMR (CDCl3): δ 8.00 (d, J=5.7 Hz, 1H), 6.08 (d, J=5.7 Hz, 1H), 4.98 (bs, 2H), 3.84 (s, 3H).

Workup

  1. filtrationwas filtered through a Celite pad
  2. customthe volatiles were removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (200 mL)
  4. washwashed with Na2CO3(sat) (100 mL) and with NaCl(sat.) (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-85c72cc0df3d4f15b906aa185dbd71ae
Source dataset
uspto-grants-2012_05
Patent number
US08173647B2

Reaction notes

Loading…