Dimethylamine → HCID 86616339, compound

HRID 2375469Notes

Reaction equation

HRID 2375469 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]=1>O1CCCC1.C(N(CC)C(C)C)(C)C>[Cl:11][C:9]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]([NH2:8])[N:6]=[C:5]([N:2]([CH3:3])[CH3:1])[CH:10]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 6171324,6-Dichloro-N-phenyl-2-pyrimidinamine

Product 1

HCID 86616339HCID 86616339, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

Dimethylamine in tetrahydrofuran (2M, 15 mL) was added to a solution of 4,6-dichloro-N-phenyl-2-pyrimidinamine (0.715 g, 2.97 mmol) in tetrahydrofuran (30 mL) and N,N-diisopropylethylamine (0.52 mL). The resulting mixture was stirred at room temperature overnight. The solvent was removed and the crude material was purified by flash chromatography on silica gel, eluting with ethyl acetate/hexane (1:9). The eluent was removed, giving 6-chloro-N4, N4-dimethyl-1-phenyl-2,4-pyrimidinediamine (0.592 g, 2.39 mmol, 80%, Rf=0.3).

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified by flash chromatography on silica gel
  3. washeluting with ethyl acetate/hexane (1:9)
  4. customThe eluent was removed

Sources & evidence

ORD record
ord-63b4db969a014282ab2b9e56f88fc53b
Source dataset
uspto-grants-2008_12
Patent number
US07465750B2

Reaction notes

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